dimethyl-carbamic acid 5-(4-chloro-phenyl)-1-[2-(4-nitro-phenoxy)-ethyl]-2,3-dihydro-1H-benzo[c]azepin-7-yl ester

Base Information

• Chemical Name: dimethyl-carbamic acid 5-(4-chloro-phenyl)-1-[2-(4-nitro-phenoxy)-ethyl]-2,3-dihydro-1H-benzo[c]azepin-7-yl ester
• CAS No.: 649723-02-4
• Molecular Formula: C₂₇H₂₆ClN₃O₅
• Molecular Weight: 507.974

Synonyms:

Chemical Property of dimethyl-carbamic acid 5-(4-chloro-phenyl)-1-[2-(4-nitro-phenoxy)-ethyl]-2,3-dihydro-1H-benzo[c]azepin-7-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of dimethyl-carbamic acid 5-(4-chloro-phenyl)-1-[2-(4-nitro-phenoxy)-ethyl]-2,3-dihydro-1H-benzo[c]azepin-7-yl ester

There total 15 articles about dimethyl-carbamic acid 5-(4-chloro-phenyl)-1-[2-(4-nitro-phenoxy)-ethyl]-2,3-dihydro-1H-benzo[c]azepin-7-yl ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

5-(4-chloro-phenyl)-7-dimethylcarbamoyloxy-1-[2-(4-nitro-phenoxy)-ethyl]-1,3-dihydro-benzo[c]azepine-2-carboxylic acid tert-butyl ester (649723-01-3) → dimethyl-carbamic acid 5-(4-chloro-phenyl)-1-[2-(4-nitro-phenoxy)-ethyl]-2,3-dihydro-1H-benzo[c]azepin-7-yl ester (649723-02-4)

Guidance literature:

With hydrogenchloride; In ethyl acetate; at 20 ℃; for 12h;

DOI:10.1016/S0968-0896(03)00452-8

Reference yield:

2,4-Dihydroxybenzaldehyde (95-01-2) → dimethyl-carbamic acid 5-(4-chloro-phenyl)-1-[2-(4-nitro-phenoxy)-ethyl]-2,3-dihydro-1H-benzo[c]azepin-7-yl ester (649723-02-4)

Guidance literature:

Multi-step reaction with 17 steps

1.1: 30 percent / NaH / dimethylformamide / 2 h / 20 °C

2.1: 4.14 g / pyridine / CH₂Cl₂ / 1 h / 0 °C

3.1: 2.11 g / Pd(PPh₃)4; LiCl; 2,6-di-t-butylphenol / dioxane / 3 h / 100 °C

4.1: lithium diisopropylamide / tetrahydrofuran; hexane / 0.33 h / -78 °C

4.2: 99 percent / tetrahydrofuran; hexane / 0.5 h / -78 °C

5.1: 97 percent / LiBH₄ / tetrahydrofuran / 1 h / 20 °C

6.1: 70 percent / 4-dimethylaminopyridine; triethylamine / CH₂Cl₂ / 5 h / 20 °C

7.1: 78 percent / triphenylphosphine; carbon tetrabromide / CH₂Cl₂ / 1 h / 20 °C

8.1: 72 percent / acetonitrile / 12 h / 20 °C

9.1: 89 percent / triethylamine / tetrahydrofuran / 3 h / 50 °C

10.1: 96 percent / (1,3-dimesitylimidazolidin-2-yl)[P(c-hexyl)3]Ru(=CHPh)Cl₂ / CH₂Cl₂ / 3 h / 45 °C

11.1: 96 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1 h / 20 °C

12.1: BH₃ / tetrahydrofuran / 15 h / 20 °C

12.2: NaBO₃*4H₂O / tetrahydrofuran; H₂O / 2 h / 20 °C

12.3: 1.87 g / manganese dioxide / CH₂Cl₂ / 2 h / 20 °C

13.1: triphenylphosphine; diethyl azodicarboxylate / tetrahydrofuran; toluene / 1 h / 20 °C

13.2: HCl / ethyl acetate / 20 °C

14.1: 1.20 g / triethylamine / tetrahydrofuran / 1 h / 20 °C

15.1: LHMDS / tetrahydrofuran / 0.5 h / -78 °C

15.2: 98 percent / tetrahydrofuran / 1 h / -78 °C

16.1: 55 percent / Pd(PPh₃)4; K₃PO₄ / dioxane / 6 h / 85 °C

17.1: HCl / ethyl acetate / 12 h / 20 °C

With pyridine; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; hydrogenchloride; dmap; potassium phosphate; lithium borohydride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; carbon tetrabromide; 2,6-di-tert-butylphenol; borane; tetrabutyl ammonium fluoride; sodium hydride; triethylamine; triphenylphosphine; lithium chloride; lithium hexamethyldisilazane; lithium diisopropyl amide; diethylazodicarboxylate; In tetrahydrofuran; 1,4-dioxane; hexane; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; toluene; acetonitrile; 3.1: Stille reaction / 13.1: Mitsunobu reaction / 16.1: Suzuki coupling;

DOI:10.1016/S0968-0896(03)00452-8

Reference yield:

4-formyl-3-hydroxy-phenyl dimethylcarbamate (444646-64-4) → dimethyl-carbamic acid 5-(4-chloro-phenyl)-1-[2-(4-nitro-phenoxy)-ethyl]-2,3-dihydro-1H-benzo[c]azepin-7-yl ester (649723-02-4)

Guidance literature:

Multi-step reaction with 16 steps

1.1: 4.14 g / pyridine / CH₂Cl₂ / 1 h / 0 °C

2.1: 2.11 g / Pd(PPh₃)4; LiCl; 2,6-di-t-butylphenol / dioxane / 3 h / 100 °C

3.1: lithium diisopropylamide / tetrahydrofuran; hexane / 0.33 h / -78 °C

3.2: 99 percent / tetrahydrofuran; hexane / 0.5 h / -78 °C

4.1: 97 percent / LiBH₄ / tetrahydrofuran / 1 h / 20 °C

5.1: 70 percent / 4-dimethylaminopyridine; triethylamine / CH₂Cl₂ / 5 h / 20 °C

6.1: 78 percent / triphenylphosphine; carbon tetrabromide / CH₂Cl₂ / 1 h / 20 °C

7.1: 72 percent / acetonitrile / 12 h / 20 °C

8.1: 89 percent / triethylamine / tetrahydrofuran / 3 h / 50 °C

9.1: 96 percent / (1,3-dimesitylimidazolidin-2-yl)[P(c-hexyl)3]Ru(=CHPh)Cl₂ / CH₂Cl₂ / 3 h / 45 °C

10.1: 96 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1 h / 20 °C

11.1: BH₃ / tetrahydrofuran / 15 h / 20 °C

11.2: NaBO₃*4H₂O / tetrahydrofuran; H₂O / 2 h / 20 °C

11.3: 1.87 g / manganese dioxide / CH₂Cl₂ / 2 h / 20 °C

12.1: triphenylphosphine; diethyl azodicarboxylate / tetrahydrofuran; toluene / 1 h / 20 °C

12.2: HCl / ethyl acetate / 20 °C

13.1: 1.20 g / triethylamine / tetrahydrofuran / 1 h / 20 °C

14.1: LHMDS / tetrahydrofuran / 0.5 h / -78 °C

14.2: 98 percent / tetrahydrofuran / 1 h / -78 °C

15.1: 55 percent / Pd(PPh₃)4; K₃PO₄ / dioxane / 6 h / 85 °C

16.1: HCl / ethyl acetate / 12 h / 20 °C

With pyridine; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; hydrogenchloride; dmap; potassium phosphate; lithium borohydride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; carbon tetrabromide; 2,6-di-tert-butylphenol; borane; tetrabutyl ammonium fluoride; triethylamine; triphenylphosphine; lithium chloride; lithium hexamethyldisilazane; lithium diisopropyl amide; diethylazodicarboxylate; In tetrahydrofuran; 1,4-dioxane; hexane; dichloromethane; ethyl acetate; toluene; acetonitrile; 2.1: Stille reaction / 12.1: Mitsunobu reaction / 15.1: Suzuki coupling;

DOI:10.1016/S0968-0896(03)00452-8

upstream raw materials:

5-(4-chloro-phenyl)-7-dimethylcarbamoyloxy-1-[2-(4-nitro-phenoxy)-ethyl]-1,3-dihydro-benzo[c]azepine-2-carboxylic acid tert-butyl ester

2,4-Dihydroxybenzaldehyde

4-formyl-3-hydroxy-phenyl dimethylcarbamate

dimethylcarbamic acid 4-formyl-3-vinylphenyl ester

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