4698-11-7

Basic information

• Product Name: 10-Methoxyiminostilbene
• Synonyms: 10-METHOXY-5H-DIBENZ[B,F]AZEPINE;10-METHOXY IMINOSTILBENE;10-Methoxyiminostibene;MethoxyIminostilbene;10-Methoxy-5H-dibenzo[b,f]azepine;10-METHOXY-5H-DIBENZO[B,F]AZEPINE,98.0+%(LC)(N);10-Methoxy-2,2'-iminostilbene;6-methoxy-11H-benzo[b][1]benzazepine
• CAS NO: 4698-11-7
• Molecular Formula: C₁₅H₁₃NO
• Molecular Weight: 223.27
• EINECS: 225-172-6
• Product Categories: Stilbenes (substituted);Aromatics Compounds;Aromatics;Heterocycles;Pharmaceutical raw material
• Mol File: 4698-11-7.mol
• Article Data: 13

Chemical Properties

• Melting Point: 122-128°C
• Boiling Point: 410.8 °C at 760 mmHg
• Flash Point: 162.5 °C
• Appearance: Yellowish foam
• Density: 1.19
• Vapor Pressure: 5.86E-07mmHg at 25°C
• Refractive Index: 1.651
• Storage Temp.: 0-10°C
• Solubility: Chloroform (Slightly), Ethyl Acetate (Slightly)
• PKA: 0.88±0.40(Predicted)
• CAS DataBase Reference: 10-Methoxyiminostilbene(CAS DataBase Reference)
• NIST Chemistry Reference: 10-Methoxyiminostilbene(4698-11-7)
• EPA Substance Registry System: 10-Methoxyiminostilbene(4698-11-7)

Safety Data

• Hazardous Substances Data: 4698-11-7(Hazardous Substances Data)

Usage

Chemical Properties

Yellowish Foam

Uses

10-Methoxy Iminostilbene exhibits antioxidant activity in vitro

InChI:InChI=1/C15H13NO/c1-17-15-10-11-6-2-4-8-13(11)16-14-9-5-3-7-12(14)15/h2-10,16H,1H3

Synthetic route

10-methoxy-5H-dibenz[b,f]azepine-5-carboxylic acid methyl ester (353497-37-7) → 10-methoxy-5H-dibenzo[b,f]azepine (4698-11-7)

Conditions	Yield
With sodium hydroxide In various solvent(s) at 100℃; for 4h;	98%
With sodium hydroxide In water	98%
With sodium hydroxide In methanol; water at 105 - 110℃; for 2.5h;	97%

10-methoxy-dibenzo[b,f]azepine-5-carboxylic acid phenyl ester (731851-94-8) → 10-methoxy-5H-dibenzo[b,f]azepine (4698-11-7)

Conditions	Yield
With sodium hydroxide In various solvent(s) at 100℃; for 4h;	96%

5-benzyl-10-methoxyiminostilbene (10465-66-4) → 10-methoxy-5H-dibenzo[b,f]azepine (4698-11-7)

Conditions	Yield
With 5%-palladium/activated carbon; hydrogen at 35 - 40℃; under 1500.15 - 2250.23 Torr; for 5h; Autoclave;	93.5%

5-acetyl-10-methoxy-5H-dibenzazepine (153261-62-2) → 10-methoxy-5H-dibenzo[b,f]azepine (4698-11-7)

Conditions	Yield
With potassium hydroxide In ethylene glycol for 5h; Heating;	80%
With triethyl borane; sodium hydroxide In tert-butyl methyl ether at 80℃; for 6h; Inert atmosphere; Sealed tube;	67%
Stage #1: 5-acetyl-10-methoxy-5H-dibenzazepine With Triethoxysilane; sodium triethylborohydride In tert-butyl methyl ether at 80℃; for 6h; Stage #2: With hydrogenchloride In tert-butyl methyl ether; water at 20℃; for 1h; chemoselective reaction;	59%

5-allyl-10-methoxy-5H-dibenzo[b,f]azepine → 10-methoxy-5H-dibenzo[b,f]azepine (4698-11-7)

Conditions	Yield
With potassium tert-butylate In dimethyl sulfoxide

5-formyl-10-bromo-11-methoxy-10,11-dihydro-5H-dibenzo[b,f]azepine → 10-methoxy-5H-dibenzo[b,f]azepine (4698-11-7)

Conditions	Yield
Stage #1: 5-formyl-10-bromo-11-methoxy-10,11-dihydro-5H-dibenzo[b,f]azepine With 1,8-diazabicyclo[5.4.0]undec-7-ene In toluene for 0.5h; Heating / reflux; Stage #2: With Deloxan ASP I/7; potassium hydroxide In toluene Product distribution / selectivity; Heating / reflux;

(2-phenylamino-phenyl)-acetic acid methyl ester (39507-06-7) → 10-methoxy-5H-dibenzo[b,f]azepine (4698-11-7)

Conditions	Yield
Multi-step reaction with 5 steps 1.1: pyridine / toluene / 24 h / 50 °C 1.2: pyridine / 22 h / 100 °C 2.1: 90 percent / aq. NaOH / methanol / 24 h / 25 °C 3.1: 70 percent / polyphosphoric acid / 3 h / 95 °C 4.1: 81 percent / p-TsOH / methanol / 5 h / Heating 5.1: 98 percent / aq. NaOH / various solvent(s) / 4 h / 100 °C View Scheme
Multi-step reaction with 6 steps 1: pyridine / toluene / 24 h / 50 °C 2: pyridine / 22 h / 100 °C 3: sodium hydroxide / water; methanol / 24 h / 20 °C 4: polyphosphoric acid / 3 h / 90 - 95 °C 5: water / 0 - 98 °C 6: sodium hydroxide / water; methanol / 2.5 h / 105 - 110 °C View Scheme

10,11-dihydro-10-oxo-5H-dibenz[b,f]azepine-5-carboxylic acid methyl ester (353497-31-1) → 10-methoxy-5H-dibenzo[b,f]azepine (4698-11-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: 81 percent / p-TsOH / methanol / 5 h / Heating 2: 98 percent / aq. NaOH / various solvent(s) / 4 h / 100 °C View Scheme
Multi-step reaction with 2 steps 1: water / 0 - 98 °C 2: sodium hydroxide / water; methanol / 2.5 h / 105 - 110 °C View Scheme

[2-(methoxycarbonyl-phenyl-amino)-phenyl]-acetic acid methyl ester (805236-74-2) → 10-methoxy-5H-dibenzo[b,f]azepine (4698-11-7)

Conditions	Yield
Multi-step reaction with 4 steps 1: 90 percent / aq. NaOH / methanol / 24 h / 25 °C 2: 70 percent / polyphosphoric acid / 3 h / 95 °C 3: 81 percent / p-TsOH / methanol / 5 h / Heating 4: 98 percent / aq. NaOH / various solvent(s) / 4 h / 100 °C View Scheme
Multi-step reaction with 4 steps 1: sodium hydroxide / water; methanol / 24 h / 20 °C 2: polyphosphoric acid / 3 h / 90 - 95 °C 3: water / 0 - 98 °C 4: sodium hydroxide / water; methanol / 2.5 h / 105 - 110 °C View Scheme

2-[(methoxycarbonyl)phenylamino]benzeneacetic acid (353497-35-5) → 10-methoxy-5H-dibenzo[b,f]azepine (4698-11-7)

Conditions	Yield
Multi-step reaction with 3 steps 1: 70 percent / polyphosphoric acid / 3 h / 95 °C 2: 81 percent / p-TsOH / methanol / 5 h / Heating 3: 98 percent / aq. NaOH / various solvent(s) / 4 h / 100 °C View Scheme
Multi-step reaction with 3 steps 1: polyphosphoric acid / 3 h / 90 - 95 °C 2: water / 0 - 98 °C 3: sodium hydroxide / water; methanol / 2.5 h / 105 - 110 °C View Scheme

10-oxo-10,11-dihydro-dibenzo[b,f]azepine-5-carboxylic acid phenyl ester → 10-methoxy-5H-dibenzo[b,f]azepine (4698-11-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: 99 percent / p-TsOH / methanol / 5 h / 60 °C 2: 96 percent / aq. NaOH / various solvent(s) / 4 h / 100 °C View Scheme

2-bromo-N,N-dimethyl benzamide (54616-47-6) → 10-methoxy-5H-dibenzo[b,f]azepine (4698-11-7)

Conditions	Yield
Multi-step reaction with 5 steps 1: 91 percent / NaOtBu / Pd(OAc)2; rac-BINAP / toluene 2: 82 percent / NaH / dimethylformamide 3: 70 percent / LDA; TMEDA; n-BuLi / tetrahydrofuran; hexane / 1 h / -20 °C 4: p-TsOH / methanol 5: t-BuOK / dimethylsulfoxide View Scheme

2-bromo-N,N-diethylbenzamide (76041-86-6) → 10-methoxy-5H-dibenzo[b,f]azepine (4698-11-7)

Conditions	Yield
Multi-step reaction with 5 steps 1: 88 percent / NaOtBu / Pd(OAc)2; rac-BINAP / toluene 2: 85 percent / NaH / dimethylformamide 3: 72 percent / LDA; TMEDA; n-BuLi / tetrahydrofuran; hexane / 2 h / -20 °C 4: p-TsOH / methanol 5: t-BuOK / dimethylsulfoxide View Scheme

o-toluidine (95-53-4) + -thiocarbamide → 10-methoxy-5H-dibenzo[b,f]azepine (4698-11-7)

Conditions	Yield
Multi-step reaction with 5 steps 1: 91 percent / NaOtBu / Pd(OAc)2; rac-BINAP / toluene 2: 82 percent / NaH / dimethylformamide 3: 70 percent / LDA; TMEDA; n-BuLi / tetrahydrofuran; hexane / 1 h / -20 °C 4: p-TsOH / methanol 5: t-BuOK / dimethylsulfoxide View Scheme
Multi-step reaction with 5 steps 1: 88 percent / NaOtBu / Pd(OAc)2; rac-BINAP / toluene 2: 85 percent / NaH / dimethylformamide 3: 72 percent / LDA; TMEDA; n-BuLi / tetrahydrofuran; hexane / 2 h / -20 °C 4: p-TsOH / methanol 5: t-BuOK / dimethylsulfoxide View Scheme

N,N-dimethyl-2-(2-toluidino)benzamide (353497-28-6) → 10-methoxy-5H-dibenzo[b,f]azepine (4698-11-7)

Conditions	Yield
Multi-step reaction with 4 steps 1: 82 percent / NaH / dimethylformamide 2: 70 percent / LDA; TMEDA; n-BuLi / tetrahydrofuran; hexane / 1 h / -20 °C 3: p-TsOH / methanol 4: t-BuOK / dimethylsulfoxide View Scheme

5,11-dihydro-5-(2-propen-1-yl)-10H-dibenz[b,f]azepin-10-one (332081-70-6) → 10-methoxy-5H-dibenzo[b,f]azepine (4698-11-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: p-TsOH / methanol 2: t-BuOK / dimethylsulfoxide View Scheme

N,N-diethyl-2-(2-toluidino)benzamide (1027035-99-9) → 10-methoxy-5H-dibenzo[b,f]azepine (4698-11-7)

Conditions	Yield
Multi-step reaction with 4 steps 1: 85 percent / NaH / dimethylformamide 2: 72 percent / LDA; TMEDA; n-BuLi / tetrahydrofuran; hexane / 2 h / -20 °C 3: p-TsOH / methanol 4: t-BuOK / dimethylsulfoxide View Scheme

2-(allyl-o-tolyl-amino)-N,N-dimethyl-benzamide (332081-66-0) → 10-methoxy-5H-dibenzo[b,f]azepine (4698-11-7)

Conditions	Yield
Multi-step reaction with 3 steps 1: 70 percent / LDA; TMEDA; n-BuLi / tetrahydrofuran; hexane / 1 h / -20 °C 2: p-TsOH / methanol 3: t-BuOK / dimethylsulfoxide View Scheme

2-(allyl-o-tolyl-amino)-N,N-diethyl-benzamide (332081-67-1) → 10-methoxy-5H-dibenzo[b,f]azepine (4698-11-7)

Conditions	Yield
Multi-step reaction with 3 steps 1: 72 percent / LDA; TMEDA; n-BuLi / tetrahydrofuran; hexane / 2 h / -20 °C 2: p-TsOH / methanol 3: t-BuOK / dimethylsulfoxide View Scheme

5-acetyl-10,11-epoxy-10,11-dihydro-5H-dibenzazepine (66849-39-6) → 10-methoxy-5H-dibenzo[b,f]azepine (4698-11-7)

Conditions	Yield
Multi-step reaction with 3 steps 1: 67 percent / LiI / CHCl3 / 0.33 h / Heating 2: 90 percent / HCl, MeOH, i-PrOH / 2 h / Heating 3: 80 percent / KOH / ethane-1,2-diol / 5 h / Heating View Scheme

N-acetyl iminostilbene (19209-60-0) → 10-methoxy-5H-dibenzo[b,f]azepine (4698-11-7)

Conditions	Yield
Multi-step reaction with 4 steps 1: 75.1 percent / NaOCl, silica gel / acetonitrile / 1.5 h / Heating 2: 67 percent / LiI / CHCl3 / 0.33 h / Heating 3: 90 percent / HCl, MeOH, i-PrOH / 2 h / Heating 4: 80 percent / KOH / ethane-1,2-diol / 5 h / Heating View Scheme

5-acetyl-10-oxo-10,11-dihydro-5H-dibenzazepine (28291-63-6) → 10-methoxy-5H-dibenzo[b,f]azepine (4698-11-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: 90 percent / HCl, MeOH, i-PrOH / 2 h / Heating 2: 80 percent / KOH / ethane-1,2-diol / 5 h / Heating View Scheme

methanol (67-56-1) + 10,11-dibromo-10,11-dihydro-5H-dibenzo[b,f]azepine-5-carbonyl chloride (40421-03-2) + sodium methylate (124-41-4) → 10-methoxy-5H-dibenzo[b,f]azepine (4698-11-7)

Conditions	Yield
Stage #1: methanol; 10,11-dibromo-10,11-dihydro-5H-dibenzo[b,f]azepine-5-carbonyl chloride; sodium methylate at 30 - 55℃; for 0.75 - 1h; Stage #2: methanol; sodium methylate at 30 - 93℃; for 12 - 16h; Product distribution / selectivity;

methyl 10-bromo-dibenz[b,f]azepine-5-carbamate (866874-00-2) → 10-methoxy-5H-dibenzo[b,f]azepine (4698-11-7)

Conditions	Yield
With sodium methylate at 20 - 93℃; for 12 - 16h; Product distribution / selectivity;

C16H14ClNO3 → 10-methoxy-5H-dibenzo[b,f]azepine (4698-11-7)

Conditions	Yield
Multi-step reaction with 5 steps 1: pyridine / 22 h / 100 °C 2: sodium hydroxide / water; methanol / 24 h / 20 °C 3: polyphosphoric acid / 3 h / 90 - 95 °C 4: water / 0 - 98 °C 5: sodium hydroxide / water; methanol / 2.5 h / 105 - 110 °C View Scheme

1-phenyl-1,3-dihydro-indol-2-one (3335-98-6) → 10-methoxy-5H-dibenzo[b,f]azepine (4698-11-7)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: sodium hydroxide / tetrahydrofuran / 5 h / 67 °C 1.2: 2 h / -10 °C 2.1: polyphosphoric acid / 3 h / 90 - 95 °C 3.1: water / 0 - 98 °C 4.1: sodium hydroxide / water; methanol / 2.5 h / 105 - 110 °C View Scheme
Multi-step reaction with 4 steps 1.1: sodium hydroxide / tetrahydrofuran / 5 h / 67 °C 1.2: 2 h / -40 °C 2.1: polyphosphoric acid / 3 h / 90 - 95 °C 3.1: water / 0 - 98 °C 4.1: sodium hydroxide / water; methanol / 2.5 h / 105 - 110 °C View Scheme
Multi-step reaction with 7 steps 1.1: sodium hydroxide / water; ethanol / 1 h / 50 °C 1.2: 4 h / 20 °C 2.1: pyridine / toluene / 24 h / 50 °C 3.1: pyridine / 22 h / 100 °C 4.1: sodium hydroxide / water; methanol / 24 h / 20 °C 5.1: polyphosphoric acid / 3 h / 90 - 95 °C 6.1: water / 0 - 98 °C 7.1: sodium hydroxide / water; methanol / 2.5 h / 105 - 110 °C View Scheme

o-cyanobromobenzene (2042-37-7) → 10-methoxy-5H-dibenzo[b,f]azepine (4698-11-7)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 5 h / 95 - 100 °C 2.1: sodium ethanolate / 2-methyltetrahydrofuran / 4 h / 50 - 60 °C 2.2: 3 h / 80 - 85 °C 3.1: potassium carbonate / methanol / 4 h / 95 - 100 °C / Autoclave 4.1: 5%-palladium/activated carbon; hydrogen / 5 h / 35 - 40 °C / 1500.15 - 2250.23 Torr / Autoclave View Scheme

2-<(phenylmethyl)amino>benzeneacetonitrile (118671-07-1) → 10-methoxy-5H-dibenzo[b,f]azepine (4698-11-7)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 5 h / 95 - 100 °C 2.1: sodium ethanolate / 2-methyltetrahydrofuran / 4 h / 50 - 60 °C 2.2: 3 h / 80 - 85 °C 3.1: potassium carbonate / methanol / 4 h / 95 - 100 °C / Autoclave 4.1: 5%-palladium/activated carbon; hydrogen / 5 h / 35 - 40 °C / 1500.15 - 2250.23 Torr / Autoclave View Scheme

N-benzyl-N-2′-cyanophenyl-2-aminophenylacetonitrile → 10-methoxy-5H-dibenzo[b,f]azepine (4698-11-7)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: sodium ethanolate / 2-methyltetrahydrofuran / 4 h / 50 - 60 °C 1.2: 3 h / 80 - 85 °C 2.1: potassium carbonate / methanol / 4 h / 95 - 100 °C / Autoclave 3.1: 5%-palladium/activated carbon; hydrogen / 5 h / 35 - 40 °C / 1500.15 - 2250.23 Torr / Autoclave View Scheme

10-methoxy-5H-dibenzo[b,f]azepine (4698-11-7) + chloroacetyl chloride (79-04-9) → 5-(chloroacetyl)-10-methoxy-5H-dibenz[b,f]azepine

Conditions	Yield
With N,N-dimethyl-aniline In tetrahydrofuran for 1h; Heating;	100%

10-methoxy-5H-dibenzo[b,f]azepine (4698-11-7) + 4-chloro-benzoyl chloride (122-01-0) → 5-(4-chlorobenzoyl)-10-methoxy-5H-dibenz[b,f]azepine

Conditions	Yield
Stage #1: 10-methoxy-5H-dibenzo[b,f]azepine With potassium hexamethylsilazane In tetrahydrofuran at 0℃; Inert atmosphere; Stage #2: 4-chloro-benzoyl chloride In tetrahydrofuran at 0 - 23℃; for 1h; Inert atmosphere;	100%

10-methoxy-5H-dibenzo[b,f]azepine (4698-11-7) → 10,11-dihydro-5H-dibenzo[b,f]azepin-10-one (21737-58-6)

Conditions	Yield
With sodium hydroxide In water at 100℃; for 4h;	98%
With hydrogenchloride; water In acetone at 20℃; for 1 - 1.5h;	97%
With hydrogenchloride In isopropyl alcohol at 25 - 65℃; for 3.25h;	93%
With hydrogenchloride In water; isopropyl alcohol at 25 - 65℃;	85.4%

10-methoxy-5H-dibenzo[b,f]azepine (4698-11-7) + acetyl chloride (75-36-5) → 5-acetyl-10-methoxy-5H-dibenzazepine (153261-62-2)

Conditions	Yield
Stage #1: 10-methoxy-5H-dibenzo[b,f]azepine With sodium hydride In N,N-dimethyl-formamide; mineral oil Inert atmosphere; Stage #2: acetyl chloride In N,N-dimethyl-formamide; mineral oil at 23℃; for 1h; Inert atmosphere;	96%

10-methoxy-5H-dibenzo[b,f]azepine (4698-11-7) + 2,4,6-trichlorobenzoyl chloride (4136-95-2) → 10-methoxy-5-(2,4,6-trichlorobenzoyl)-5H-dibenz[b,f]azepine

Conditions	Yield
Stage #1: 10-methoxy-5H-dibenzo[b,f]azepine With potassium hexamethylsilazane In tetrahydrofuran at 0℃; Inert atmosphere; Stage #2: 2,4,6-trichlorobenzoyl chloride In tetrahydrofuran at 0 - 23℃; for 1h; Inert atmosphere;	96%

10-methoxy-5H-dibenzo[b,f]azepine (4698-11-7) + mesitylene-2-carboxylic acid chloride (938-18-1) → 10-methoxy-5-(2,4,6-trimethylbenzoyl)-5H-dibenz[b,f]azepine

Conditions	Yield
Stage #1: 10-methoxy-5H-dibenzo[b,f]azepine With potassium hexamethylsilazane In tetrahydrofuran at 0℃; Inert atmosphere; Stage #2: mesitylene-2-carboxylic acid chloride In tetrahydrofuran at 0 - 23℃; for 1h; Inert atmosphere;	95%

10-methoxy-5H-dibenzo[b,f]azepine (4698-11-7) + allyl bromide (106-95-6) → 5,11-dihydro-5-(2-propen-1-yl)-10H-dibenz[b,f]azepin-10-one (332081-70-6)

Conditions	Yield
Stage #1: 10-methoxy-5H-dibenzo[b,f]azepine With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 0.5h; Stage #2: allyl bromide In N,N-dimethyl-formamide; mineral oil at 20℃; for 4h; Stage #3: With hydrogenchloride In water; N,N-dimethyl-formamide; mineral oil for 1h;	94%

10-methoxy-5H-dibenzo[b,f]azepine (4698-11-7) + bis(trichloromethyl) carbonate (32315-10-9) → 10-methoxy-5H-dibenz[b,f]azepine-5-carboxamide (28721-09-7)

Conditions	Yield
Stage #1: 10-methoxy-5H-dibenzo[b,f]azepine; bis(trichloromethyl) carbonate With triethylamine In toluene at 10 - 15℃; for 6h; Stage #2: With ammonia In water; toluene at 20℃; for 1h;	85%

10-methoxy-5H-dibenzo[b,f]azepine (4698-11-7) + bis(trichloromethyl) carbonate (32315-10-9) → 10-methoxyiminostilbene carbonyl chloride (28721-08-6)

Conditions	Yield
With 2,3-Dimethylaniline In chloroform at 0 - 10℃; for 6h; Product distribution / selectivity;	82%
With triethylamine In chloroform at 0 - 30℃; for 10 - 14h; Product distribution / selectivity;	80%
With triethylamine In 1,2-dichloro-ethane at 0 - 20℃; for 16h;	57%

10-methoxy-5H-dibenzo[b,f]azepine (4698-11-7) + sodium isocyanate (917-61-3) → oxcarbazepine (28721-07-5)

Conditions	Yield
With hydrogenchloride	80%
Stage #1: 10-methoxy-5H-dibenzo[b,f]azepine; sodium isocyanate With water; Pyridine hydrobromide In toluene at 22℃; for 7 - 8h; Stage #2: With hydrogenchloride In water; toluene at 55 - 89℃; for 3 - 4h; Heating / reflux;	44%
Stage #1: 10-methoxy-5H-dibenzo[b,f]azepine; sodium isocyanate With water; quinoline hydrochloride In toluene at 20℃; for 18h; Stage #2: With hydrogenchloride In water; toluene at 89℃; for 2h; Heating / reflux;	35%
Stage #1: 10-methoxy-5H-dibenzo[b,f]azepine; sodium isocyanate With acetic acid at 25 - 35℃; for 1.33333 - 1.5h; Stage #2: With sulfuric acid; water at 33 - 35℃; for 1 - 2h;

10-methoxy-5H-dibenzo[b,f]azepine (4698-11-7) + 9-fluorenylmethoxycarbonyl isocyanate (232951-82-5) → 10-methoxy-5H-dibenz[b,f]azepine-5-carboxamide (28721-09-7)

Conditions	Yield
Stage #1: 10-methoxy-5H-dibenzo[b,f]azepine; 9-fluorenylmethoxycarbonyl isocyanate In dichloromethane at 20℃; for 16h; Inert atmosphere; Stage #2: With piperidine In dichloromethane Inert atmosphere;	80%

10-methoxy-5H-dibenzo[b,f]azepine (4698-11-7) + bis(trichloromethyl) carbonate (32315-10-9) → oxcarbazepine (28721-07-5)

Conditions	Yield
Stage #1: 10-methoxy-5H-dibenzo[b,f]azepine; bis(trichloromethyl) carbonate With triethylamine In toluene at 10 - 15℃; for 6h; Stage #2: With ammonia In water; toluene at 20℃; for 1h; Stage #3: With formic acid; water for 1h; Product distribution / selectivity; Heating / reflux;	76.6%
Stage #1: 10-methoxy-5H-dibenzo[b,f]azepine; bis(trichloromethyl) carbonate With pyridine In toluene at 10 - 15℃; for 6h; Stage #2: With ammonia In water; toluene at 20℃; for 1h; Stage #3: With sulfuric acid; water for 1h; Product distribution / selectivity; Heating / reflux;	72.7%
Stage #1: 10-methoxy-5H-dibenzo[b,f]azepine; bis(trichloromethyl) carbonate With triethylamine In dichloromethane Heating / reflux; Stage #2: With ammonia In dichloromethane; water at 20℃; for 1h; Stage #3: With sulfuric acid; water for 1h; Product distribution / selectivity; Heating / reflux;	68.7%
Stage #1: 10-methoxy-5H-dibenzo[b,f]azepine; bis(trichloromethyl) carbonate With 1,4-diaza-bicyclo[2.2.2]octane In toluene at 10 - 15℃; for 6h; Stage #2: With ammonia In water; toluene at 20℃; for 1h; Stage #3: With formic acid; water for 1h; Product distribution / selectivity; Heating / reflux;	67.3%
Stage #1: 10-methoxy-5H-dibenzo[b,f]azepine; bis(trichloromethyl) carbonate With triethylamine In toluene at 10 - 15℃; for 2 - 6h; Stage #2: With ammonia In water; toluene at 20℃; for 1h; Stage #3: With sulfuric acid; water for 1h; Product distribution / selectivity; Heating / reflux;	64%

bromobenzene (108-86-1) + 10-methoxy-5H-dibenzo[b,f]azepine (4698-11-7) → C21H17NO

Conditions	Yield
With potassium tert-butylate; copper(II) oxide In dimethyl sulfoxide at 100℃; for 18h; Reagent/catalyst; Inert atmosphere;	69%
With potassium tert-butylate; copper(II) oxide In dimethyl sulfoxide at 100℃; for 18h; Solvent; Sealed tube; Inert atmosphere;	69%
With nickel(II) oxide; potassium tert-butylate; triphenylphosphine In tetrahydrofuran at 120℃; for 24h; Inert atmosphere; Sealed tube; Green chemistry;	63%

iodobenzene (591-50-4) + 10-methoxy-5H-dibenzo[b,f]azepine (4698-11-7) → C21H17NO

Conditions	Yield
With potassium tert-butylate; copper(II) oxide In N,N-dimethyl-formamide at 100℃; for 18h; Solvent; Sealed tube; Inert atmosphere;	64%
With potassium tert-butylate; copper(II) oxide In dimethyl sulfoxide at 100℃; for 18h; Reagent/catalyst; Inert atmosphere;	63%
With nickel(II) oxide; potassium tert-butylate; triphenylphosphine In tetrahydrofuran at 120℃; for 24h; Inert atmosphere; Sealed tube; Green chemistry;	57%

10-methoxy-5H-dibenzo[b,f]azepine (4698-11-7) + chlorobenzene (108-90-7) → C21H17NO

Conditions	Yield
With potassium tert-butylate; copper(II) oxide In dimethyl sulfoxide at 100℃; for 18h; Inert atmosphere;	59%
With potassium tert-butylate; copper(II) oxide In dimethyl sulfoxide at 100℃; for 18h; Solvent; Sealed tube; Inert atmosphere;	59%

10-methoxy-5H-dibenzo[b,f]azepine (4698-11-7) + 9-fluorenylmethoxycarbonyl isothiocyanate (199915-38-3) → 10-methoxy-5H-dibenz[b,f]azepine-5-carbothioamide

Conditions	Yield
Stage #1: 10-methoxy-5H-dibenzo[b,f]azepine; 9-fluorenylmethoxycarbonyl isothiocyanate In dichloromethane at 80℃; for 24h; Inert atmosphere; Stage #2: With piperidine In dichloromethane	57%

bromobenzene (108-86-1) + 10-methoxy-5H-dibenzo[b,f]azepine (4698-11-7) → 5-(4-bromophenyl)-10-methoxy-5H-dibenzo[b,f]azepine

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate In toluene for 8h; Inert atmosphere; Reflux;	54%

10-methoxy-5H-dibenzo[b,f]azepine (4698-11-7) + sodium isocyanate (917-61-3) → 10-methoxy-5H-dibenz[b,f]azepine-5-carboxamide (28721-09-7)

Conditions	Yield
Stage #1: 10-methoxy-5H-dibenzo[b,f]azepine; sodium isocyanate With pyridinium p-toluenesulfonate In acetonitrile at 20℃; for 4h; Stage #2: With water In acetonitrile at 20℃; for 0.25h;	50%
With acetic acid at 25℃; for 7h;
Stage #1: 10-methoxy-5H-dibenzo[b,f]azepine; sodium isocyanate With Pyridine hydrobromide In toluene at 22℃; for 7 - 8h; Stage #2: With water In toluene for 0.25h;

10-methoxy-5H-dibenzo[b,f]azepine (4698-11-7) + 1,4-bromoiodobenzene (589-87-7) → 5-(4-bromophenyl)-10-methoxy-5H-dibenzo[b,f]azepine

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate In toluene for 8h; Buchwald-Hartwig Coupling; Reflux; Inert atmosphere;	50%

10-methoxy-5H-dibenzo[b,f]azepine (4698-11-7) → oxcarbazepine (28721-07-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: AcOH / 7 h / 25 °C 2: H2SO4 / 17 h / 25 °C View Scheme
With hydrogenchloride; benzoic acid In water; toluene
With sulfuric acid In water; toluene
Multi-step reaction with 2 steps 1: acetic acid / 6.17 h / 20 - 45 °C / Inert atmosphere 2: hydrogenchloride / water; acetone / 2 h / 40 °C View Scheme

Upstream product

• 153261-62-2 5-acetyl-10-methoxy-5H-dibenzazepine 
• 19209-60-0 N-acetyl iminostilbene 
• 866874-00-2 methyl 10-bromo-dibenz[b,f]azepine-5-carbamate 
• 67-56-1 methanol 
• 40421-03-2 10,11-dibromo-10,11-dihydro-5H-dibenzo[b,f]azepine-5-carbonyl chloride 
• 124-41-4 sodium methylate 
• 28291-63-6 5-acetyl-10-oxo-10,11-dihydro-5H-dibenzazepine 
• 66849-39-6 5-acetyl-10,11-epoxy-10,11-dihydro-5H-dibenzazepine 
• 332081-67-1 2-(allyl-o-tolyl-amino)-N,N-diethyl-benzamide 
• 332081-66-0 2-(allyl-o-tolyl-amino)-N,N-dimethyl-benzamide 
• 95-53-4 o-toluidine 
• 76041-86-6 2-bromo-N,N-diethylbenzamide 
• 54616-47-6 o-bromo-N,N'-dimethylbenzamide 
• 353497-35-5 2-[(methoxycarbonyl)phenylamino]benzeneacetic acid 

Downstream Products

• 28721-07-5 oxcarbazepine 
• 28721-09-7 10-methoxy-5H-dibenz[b,f]azepine-5-carboxamide 
• 21737-58-6 10,11-dihydro-5H-dibenzo[b,f]azepin-10-one 
• 153261-62-2 5-acetyl-10-methoxy-5H-dibenzazepine 
• 98253-74-8 10,11-dihydro-10-methoxy-5H-dibenzo[b,f]azepine-5-carboxamide 
• 4014-77-1 10,11-dihydro-5H-dibenzo[b,f]azepin-10-ol?? 
• 186694-45-1 eslicarbazepine acetate 
• 256-96-2 dibenzoazepine 
• 298-46-4 carbamazepin 
• 28721-08-6 10-methoxyiminostilbene carbonyl chloride 

Relevant articles and documents

Combined KOH/BEt3Catalyst for Selective Deaminative Hydroboration of Aromatic Carboxamides for Construction of Luminophores

The selective catalytic C-N bond cleavage of amides into value-added amine products is a desirable but challenging transformation. Molecules containing iminodibenzyl motifs are prevalent in pharmaceutical molecules and functional materials. Here we established a combined KOH/BEt3 catalyst for deaminative hydroboration of acyl-iminodibenzyl derivatives, including nonheterocyclic carboxamides, to the corresponding amines. This novel transition-metal-free methodology was also applied to the construction of Clomipramine and luminophores.

Hydride-catalyzed selectively reductive cleavage of unactivated tertiary amides using hydrosilane

The first hydride-catalyzed reductive cleavage of various unactivated tertiary amides, including the biologically active aryl-phenazine carboxamides and the challenging non-heterocyclic carbonyl functions, using low-cost hydrosilane as a reducing reagent has been developed. The novel catalyst system exhibits high efficiency and exclusive selectivity, providing the desired amines in useful to excellent yields under mild conditions. Overall, this transition metal-free process may offer a versatile alternative to currently employed expensive reducing reagents, high-pressure hydrogen or metal systems for the selective reductive cleavage of amides.

A new industrial process for 10-methoxyiminostilbene: Key intermediate for the synthesis of oxcarbazepine

A new industrial process, involving only two isolation and drying steps, for 10-methoxyiminostilbene (MISB), an advance intermediate of widely prescribed antiepileptic drug, oxcarbazepine, has been developed. A salient feature of this process is the novel use of 1,3-dibromo-5,5-dimethylhydantoin (DBDMH) to afford bro-mohydrin methyl ether from N-acetyliminostilbene. The byproducts of this process namely acetic acid, 5,5-dimethylhydantoin and Et3N HBr are recyclable as well as nontoxic This process is amenable for the large-scale production of MISB.