83857-96-9

Basic information

• Product Name: 2-Butyl-4-chloro-5-formylimidazole
• Synonyms: 2-BUTYL-5-CHLOROIMIDAZOLE-4-CARBOXALDEHYDE;2-BUTYL-4-CHLORO-IMIDAZOLE-5-CARBALDEHYDE;2-BUTYL-5-CHLORO-1H-IMIDAZOLE-4-CARBALDEHYDE;2-BUTYL-5-CHLORO-1H-IMIDAZOLE-4-CARBOXALDEHYDE;2-BUTYL-4-CHLORO-1H-IMIDAZOLE-5-CARBALDEHYDE;2-BUTYL-4-CHLORO-1H-IMIDAZOLE-5-CARBOXALDEHYDE;2-BUTYL-4-CHLORO-5-FORMYLIMIDAZLOE;2-BUTYL-4-CHLORO-5-FORMYLIMIDAZOLE
• CAS NO: 83857-96-9
• Molecular Formula: C₈H₁₁ClN₂O
• Molecular Weight: 186.64
• EINECS: 410-260-0
• Product Categories: INTERMEDIATESOF;Aldehydes;Imidazoles & Benzimidazoles;(intermediate of losartan);Heterocyclic Compounds;Hypertension;Heterocycles;Imidazoles & Benzimidazoles;Building Blocks;C8;Carbonyl Compounds;Chemical Synthesis;Halogenated Heterocycles;Heterocyclic Building Blocks;Imidazoles;Organic Building Blocks;api;Intermediates
• Mol File: 83857-96-9.mol
• Article Data: 36

Chemical Properties

• Melting Point: 97-100 °C(lit.)
• Boiling Point: 384.1 °C at 760 mmHg
• Flash Point: 186.1 °C
• Appearance: Yellow solid
• Density: 1.240
• Vapor Pressure: 0.001Pa at 25℃
• Storage Temp.: Refrigerator
• Solubility: slightly soluble
• PKA: 8.87±0.10(Predicted)
• Water Solubility: slightly soluble
• CAS DataBase Reference: 2-Butyl-4-chloro-5-formylimidazole(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Butyl-4-chloro-5-formylimidazole(83857-96-9)
• EPA Substance Registry System: 2-Butyl-4-chloro-5-formylimidazole(83857-96-9)

Safety Data

• Hazard Codes: Xi,N
• Statements: 43-51/53
• Safety Statements: 24-37-61
• RIDADR: UN 3077 9/PG 3
• WGK Germany: 2
• HazardClass: IRRITANT
• PackingGroup: III
• Hazardous Substances Data: 83857-96-9(Hazardous Substances Data)

Usage

Chemical Properties

2-Butyl-4-chloro-5-formylimidazole is Yellow Solid

Uses

2-Butyl-4-chloro-5-formylimidazole is used for preparation of N-(biphenylylmethyl)imidazoles as angiotensin II antagonists

Uses

2-Butyl-5-chloro-1H-imidazole-4-carboxaldehyde may be used in the preparation of the following symmetrical esters of dialkyl 4-(2-butyl-5-chloro-1H-imidazol-4-yl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate:dimethyl 4-(2-butyl-5-chloro-1H-imidazol-4-yl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylatediethyl 4-(2-butyl-5-chloro-1H-imidazol-4-yl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylatediisopropyl 4-(2-butyl-5-chloro-1Himidazol-4-yl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylatediisobutyl 4-(2-butyl-5-chloro-1H-imidazol-4-yl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate di-tert-butyl 4-(2-butyl-5-chloro-1Himidazol-4-yl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylatebis(2-methoxyethyl) 4-(2-butyl-5-chloro-1Himidazol-4-yl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate

Application

2-Butyl-4-chloro-1H-imidazole-5-carboxaldehyde (Losartan EP Impurity D) is used for preparation of N-(biphenylylmethyl)imidazoles as angiotensin II antagonists. Losartan USP Related Compound A.

Synthesis Reference(s)

The Journal of Organic Chemistry, 64, p. 8084, 1999 DOI: 10.1021/jo9824910

InChI:InChI=1/C8H11ClN2O/c1-2-3-4-7-10-6(5-12)8(9)11-7/h5H,2-4H2,1H3,(H,10,11)

Synthetic route

(NH4)2 Ce(NO3)6 + dichloromethane (75-09-2) + 2-n-butyl-4-chloro-5-hydroxymethylimidazole (79047-41-9) → 2-n-butyl-4-chloro-1H-imidazol-5-carboxaldehyde (83857-96-9)

Conditions	Yield
With potassium hydroxide In water; acetic acid	92%
In water; acetic acid

(1-iminopentyl)glycine tert-butyl ester + N,N-dimethyl-formamide (68-12-2, 33513-42-7) → 2-n-butyl-4-chloro-1H-imidazol-5-carboxaldehyde (83857-96-9)

Conditions	Yield
Stage #1: (1-iminopentyl)glycine tert-butyl ester With trifluoroacetic acid In 1,2-dichloro-ethane at 20℃; for 24h; Large scale; Stage #2: With trichlorophosphate In toluene at 80℃; for 2h; Large scale; Stage #3: N,N-dimethyl-formamide In toluene at 105℃; for 7h; Temperature; Large scale;	89.2%

(Z)-2-butyl-4-(dimethylaminomethylene)-2-imidazolin-5-one (168900-00-3) → 2-n-butyl-4-chloro-1H-imidazol-5-carboxaldehyde (83857-96-9)

Conditions	Yield
With trichlorophosphate at 100℃; for 1.5h; Substitution;	88%

4(5)-bromo-2-butyl-1H-imidazole-5(4)-carboxaldehyde (139742-78-2) → 2-n-butyl-4-chloro-1H-imidazol-5-carboxaldehyde (83857-96-9)

Conditions	Yield
With hydrogenchloride for 24h; Heating;	87%

2-n-butyl-4-chloro-5-hydroxymethylimidazole (79047-41-9) → 2-n-butyl-4-chloro-1H-imidazol-5-carboxaldehyde (83857-96-9)

Conditions	Yield
With ammonium cerium(IV) nitrate In acetic acid at 25℃; for 3h;	77%
With 2,2,6,6-tetramethyl-piperidine-N-oxyl; iodine; sodium hydrogencarbonate In water; toluene at 20℃; for 16h;	690 mg
With oxygen; Pt/Bi on graphite In methanol at 60℃; under 2250.23 Torr; for 6h; Product distribution; Further Variations:; Reagents;
With manganese dioxide In dichloromethane	12.81 g (86%)

methyl pentanimidate (57246-71-6) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) + glycine (56-40-6) → 2-n-butyl-4-chloro-1H-imidazol-5-carboxaldehyde (83857-96-9)

Conditions	Yield
Stage #1: glycine With sodium hydroxide In methanol at 0℃; for 0.25h; Stage #2: methyl pentanimidate In methanol at 0 - 20℃; for 16.16 - 16.25h; Stage #3: N,N-dimethyl-formamide With sodium hydroxide; water; trichlorophosphate; copper(II) bis(trifluoromethanesulfonate) Product distribution / selectivity; more than 3 stages;	71%
Stage #1: glycine With sodium hydroxide In methanol at 0℃; for 0.25h; Stage #2: methyl pentanimidate In methanol at 0 - 20℃; for 16.16 - 16.25h; Stage #3: N,N-dimethyl-formamide With sodium hydroxide; trichlorophosphate Product distribution / selectivity; more than 3 stages;	66.4%
Stage #1: methyl pentanimidate; glycine With sodium hydroxide In methanol; water; toluene Stage #2: N,N-dimethyl-formamide With trichlorophosphate In toluene at 100℃; for 2h;	55%

N,N-dimethyl-formamide (68-12-2, 33513-42-7) + 2-butyl-2-imidazolin-5-one (154147-42-9) → 2-n-butyl-4-chloro-1H-imidazol-5-carboxaldehyde (83857-96-9) + (E)-2-(but-1-en-1-yl)-5-chloroimidazole-4-carbaldehyde + 5-chloro-2-(2-chlorobutyl)imidazole-4-carbaldehyde

Conditions	Yield
With trichlorophosphate In toluene at 100℃; for 2h; Dehydrogenation; Vilsmeier formylation; chlorination;	A 55% B n/a C n/a

[2-Butyl-5-chloro-imidazol-(4Z)-ylidenemethyl]-dimethyl-amine → 2-n-butyl-4-chloro-1H-imidazol-5-carboxaldehyde (83857-96-9)

Conditions	Yield
With water Yield given;
With water Hydrolysis; Acid hydrolysis;

2-butyl-1H-imidazole-5-carboxaldehyde (68282-49-5) → 2-n-butyl-4-chloro-1H-imidazol-5-carboxaldehyde (83857-96-9)

Conditions	Yield
With N-chloro-succinimide Chlorination;

N,N-dimethyl-formamide (68-12-2, 33513-42-7) + 2-butyl-5-chloro-1H-imidazole (158365-99-2) → 2-n-butyl-4-chloro-1H-imidazol-5-carboxaldehyde (83857-96-9)

Conditions	Yield
With trichlorophosphate In chlorobenzene at 100℃; for 4h; Formylation; Vilsmeier reaction;

N,N-dimethyl-formamide (68-12-2, 33513-42-7) + (pentanimidoylamino)acetic acid (193140-43-1) → 2-n-butyl-4-chloro-1H-imidazol-5-carboxaldehyde (83857-96-9)

Conditions	Yield
With trichlorophosphate In toluene at 100℃; for 2h; Cyclization; Vilsmeier formylation; substitution;	26.0 g
With trichlorophosphate In toluene at 97 - 100℃; for 3h;	132 g
With trichlorophosphate In toluene at 60 - 100℃; for 2h; Green chemistry;	0.154 g

2-n-butyl-4-chloro-5-hydroxymethylimidazole (79047-41-9) → 2-n-butyl-4-chloro-1H-imidazol-5-carboxaldehyde (83857-96-9) + 2-butyl-4,5-dichloroimidazole

Conditions	Yield
With 2,2,6,6-tetramethyl-piperidine-N-oxyl; N-chloro-succinimide; sodium hydrogencarbonate In water; toluene at 20℃;	A n/a B 85 % Chromat.

2-n-butyl-4-chloro-5-hydroxymethylimidazole (79047-41-9) → 2-n-butyl-4-chloro-1H-imidazol-5-carboxaldehyde (83857-96-9) + 5-bromo-2-butyl-4-chloro-1H-imidazole

Conditions	Yield
With 2,2,6,6-tetramethyl-piperidine-N-oxyl; N-Bromosuccinimide; sodium hydrogencarbonate In water; toluene at 20℃;	A n/a B 85 % Chromat.

pentanonitrile (110-59-8) → 2-n-butyl-4-chloro-1H-imidazol-5-carboxaldehyde (83857-96-9)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: HCl / 12 h / 20 °C 1.2: aq. KOH / toluene / 5 °C 2.1: aq. KOH / toluene; methanol / 15 h / 40 °C 3.1: 132 g / POCl3 / toluene / 3 h / 97 - 100 °C View Scheme
Multi-step reaction with 4 steps 1: 190.8 g / HCl / dibutyl ether / 144 h / 4 °C 2: 95 percent / NaOH / methanol; toluene / 3 h / 20 °C 3: 44 percent / CH2Cl2 / 20 - 27 °C 4: 88 percent / POCl3 / 1.5 h / 100 °C View Scheme
Multi-step reaction with 5 steps 1: 190.8 g / HCl / dibutyl ether / 144 h / 4 °C 2: 95 percent / NaOH / methanol; toluene / 3 h / 20 °C 3: 31 percent / POCl3 / chlorobenzene / 2 h / 100 °C 4: Et3N / chlorobenzene / Heating 5: H2O / Acid hydrolysis View Scheme

methyl pentanimidate (57246-71-6) → 2-n-butyl-4-chloro-1H-imidazol-5-carboxaldehyde (83857-96-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: aq. KOH / toluene; methanol / 15 h / 40 °C 2: 132 g / POCl3 / toluene / 3 h / 97 - 100 °C View Scheme
Multi-step reaction with 3 steps 1: 95 percent / NaOH / methanol; toluene / 3 h / 20 °C 2: 44 percent / CH2Cl2 / 20 - 27 °C 3: 88 percent / POCl3 / 1.5 h / 100 °C View Scheme
Multi-step reaction with 4 steps 1: 95 percent / NaOH / methanol; toluene / 3 h / 20 °C 2: 31 percent / POCl3 / chlorobenzene / 2 h / 100 °C 3: Et3N / chlorobenzene / Heating 4: H2O / Acid hydrolysis View Scheme

pentanimidamide (109-51-3) → 2-n-butyl-4-chloro-1H-imidazol-5-carboxaldehyde (83857-96-9)

Conditions	Yield
Multi-step reaction with 3 steps 2: 44 percent / CH2Cl2 / 20 - 27 °C 3: 88 percent / POCl3 / 1.5 h / 100 °C View Scheme
Multi-step reaction with 4 steps 2: 31 percent / POCl3 / chlorobenzene / 2 h / 100 °C 3: Et3N / chlorobenzene / Heating 4: H2O / Acid hydrolysis View Scheme
Multi-step reaction with 3 steps 2: 31 percent / POCl3 / chlorobenzene / 2 h / 100 °C 3: POCl3 / chlorobenzene / 4 h / 100 °C View Scheme

ethyl valerimidate (999-09-7) → 2-n-butyl-4-chloro-1H-imidazol-5-carboxaldehyde (83857-96-9)

Conditions	Yield
Multi-step reaction with 3 steps 1: 40 percent / 24 h / -10 °C 2: 44 percent / CH2Cl2 / 20 - 27 °C 3: 88 percent / POCl3 / 1.5 h / 100 °C View Scheme
Multi-step reaction with 4 steps 1: 40 percent / 24 h / -10 °C 2: 31 percent / POCl3 / chlorobenzene / 2 h / 100 °C 3: Et3N / chlorobenzene / Heating 4: H2O / Acid hydrolysis View Scheme
Multi-step reaction with 3 steps 1: 40 percent / 24 h / -10 °C 2: 31 percent / POCl3 / chlorobenzene / 2 h / 100 °C 3: POCl3 / chlorobenzene / 4 h / 100 °C View Scheme

2-butyl-2-imidazolin-5-one (154147-42-9) → 2-n-butyl-4-chloro-1H-imidazol-5-carboxaldehyde (83857-96-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: 44 percent / CH2Cl2 / 20 - 27 °C 2: 88 percent / POCl3 / 1.5 h / 100 °C View Scheme
Multi-step reaction with 3 steps 1: 31 percent / POCl3 / chlorobenzene / 2 h / 100 °C 2: Et3N / chlorobenzene / Heating 3: H2O / Acid hydrolysis View Scheme
Multi-step reaction with 2 steps 1: 31 percent / POCl3 / chlorobenzene / 2 h / 100 °C 2: POCl3 / chlorobenzene / 4 h / 100 °C View Scheme
Multi-step reaction with 2 steps 1: 1.) POCl3 / 1.) toluene, 80 deg C, 2.) toluene, 100 deg C 2: H2O View Scheme

2-butyl-5-chloro-1H-imidazole (158365-99-2) → 2-n-butyl-4-chloro-1H-imidazol-5-carboxaldehyde (83857-96-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: Et3N / chlorobenzene / Heating 2: H2O / Acid hydrolysis View Scheme

2-butyl-1H-imidazole (50790-93-7) → 2-n-butyl-4-chloro-1H-imidazol-5-carboxaldehyde (83857-96-9)

Conditions	Yield
Multi-step reaction with 3 steps 1: H2O 2: MnO2 / CH2Cl2 3: N-chlorosuccinimide View Scheme
Multi-step reaction with 5 steps 1: 56 percent / Br2 / CHCl3 / Ambient temperature 2: 85 percent / Na2SO3 / H2O; ethanol / 18 h / Heating 3: 78 percent / aq. NaOH / ethanol / Ambient temperature 4: 81 percent / MnO2 / CH2Cl2; dioxane / Heating 5: 87 percent / conc. aq. HCl / 24 h / Heating View Scheme

2-butyl-5-hydroxymethyl-1H-imidazole (68283-19-2) → 2-n-butyl-4-chloro-1H-imidazol-5-carboxaldehyde (83857-96-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: MnO2 / CH2Cl2 2: N-chlorosuccinimide View Scheme

4(5)-bromo-2-butyl-1H-imidazole (145575-93-5) → 2-n-butyl-4-chloro-1H-imidazol-5-carboxaldehyde (83857-96-9)

Conditions	Yield
Multi-step reaction with 3 steps 1: 78 percent / aq. NaOH / ethanol / Ambient temperature 2: 81 percent / MnO2 / CH2Cl2; dioxane / Heating 3: 87 percent / conc. aq. HCl / 24 h / Heating View Scheme

4,5-dibromo-2-butyl-1H-imidazole (145575-92-4) → 2-n-butyl-4-chloro-1H-imidazol-5-carboxaldehyde (83857-96-9)

Conditions	Yield
Multi-step reaction with 4 steps 1: 85 percent / Na2SO3 / H2O; ethanol / 18 h / Heating 2: 78 percent / aq. NaOH / ethanol / Ambient temperature 3: 81 percent / MnO2 / CH2Cl2; dioxane / Heating 4: 87 percent / conc. aq. HCl / 24 h / Heating View Scheme

4(5)-bromo-2-butyl-1H-imidazole-5(4)-methanol (139742-77-1) → 2-n-butyl-4-chloro-1H-imidazol-5-carboxaldehyde (83857-96-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: 81 percent / MnO2 / CH2Cl2; dioxane / Heating 2: 87 percent / conc. aq. HCl / 24 h / Heating View Scheme

aqueous H2 O2 + water (7732-18-5) + 2-n-butyl-4-chloro-5-hydroxymethylimidazole (79047-41-9) → 2-n-butyl-4-chloro-1H-imidazol-5-carboxaldehyde (83857-96-9)

Conditions	Yield
With hydrogenchloride; sodium hydroxide In methanol
With hydrogenchloride; sodium hydroxide In methanol

aqueous H2 O2 + 2-n-butyl-4-chloro-5-hydroxymethylimidazole (79047-41-9) + 4-methyl-2-pentanone (108-10-1) → 2-n-butyl-4-chloro-1H-imidazol-5-carboxaldehyde (83857-96-9)

Conditions	Yield
With hydrogenchloride; sodium hydroxide In water

2-butyl-4-chloro-5-hydroxyimdazole → 2-n-butyl-4-chloro-1H-imidazol-5-carboxaldehyde (83857-96-9)

Conditions	Yield
With manganese dioxide; silica gel In methanol

Cs2 CO3 + dichloromethane (75-09-2) + Ethyl 4-(bromomethyl)benzoate (26496-94-6) + 2-n-butyl-4-chloro-5-hydroxymethylimidazole (79047-41-9) → 2-n-butyl-4-chloro-1H-imidazol-5-carboxaldehyde (83857-96-9)

Conditions	Yield
With manganese dioxide In tetrahydrofuran; methanol; water; ethyl acetate; N,N-dimethyl-formamide

1H-imidazole (288-32-4) + 2-n-butyl-4-chloro-5-hydroxymethylimidazole (79047-41-9) → 2-n-butyl-4-chloro-1H-imidazol-5-carboxaldehyde (83857-96-9)

Conditions	Yield
With NH4Ca(NO3)3; sodium hydroxide In acetic acid
With NH4Ca(NO3)3; sodium hydroxide In acetic acid

2-n-butyl-4-chloro-1H-imidazol-5-carboxaldehyde (83857-96-9) + N-(triphenylmethyl)-5-<4'-(bromomethyl)biphenyl-2-yl>tetrazole (133051-88-4) → 2-n-butyl-4-chloro-1-[(2'-(2-triphenylmethyl-2H-tetrazol-5-yl)-1,1'-biphenyl-4-yl)methyl]-1H-imidazole-5-methanol (133909-99-6)

Conditions	Yield
Stage #1: 2-n-butyl-4-chloro-1H-imidazol-5-carboxaldehyde; N-(triphenylmethyl)-5-<4'-(bromomethyl)biphenyl-2-yl>tetrazole With potassium carbonate In N,N-dimethyl-formamide at 20 - 22℃; for 3h; Stage #2: With sodium tetrahydroborate In water; N,N-dimethyl-formamide at 48 - 52℃; for 3.08333h;	99.2%
With potassium carbonate In N,N-dimethyl acetamide
With potassium carbonate In N,N-dimethyl acetamide

1H-benzimidazol-2-acetonitrile (4414-88-4) + 2-n-butyl-4-chloro-1H-imidazol-5-carboxaldehyde (83857-96-9) → (E)-2-(1H-benzo[d]imidazol-2-yl)-3-(2-butyl-4-chloro-1H-imidazol-5-yl)acrylonitrile

Conditions	Yield
With L-proline In ethanol at 20℃; for 0.166667h; Knoevenagel Condensation;	98%

2-n-butyl-4-chloro-1H-imidazol-5-carboxaldehyde (83857-96-9) → 2-n-butyl-5-chloro-3H-imidazole-4-carboxylic acid

Conditions	Yield
With sodium chlorite; sodium dihydrogen phosphate monohydrate; 2-methyl-but-2-ene In tetrahydrofuran; water; tert-butyl alcohol at 20℃; for 12h;	95%
Multi-step reaction with 2 steps 1.1: sodium cyanide; manganese(IV) oxide; acetic acid / 20 h / 60 °C 2.1: sodium hydroxide / ethanol; water / 2.5 h / Reflux 2.2: pH 3 - 4 View Scheme

benzyl bromide (100-39-0) + 2-n-butyl-4-chloro-1H-imidazol-5-carboxaldehyde (83857-96-9) → 3-benzyl-2-butyl-5-chloro-3H-imidazole-4-carbaldehyde (141692-01-5)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 0 - 20℃; for 4h;	92%
With potassium carbonate In N,N-dimethyl-formamide at 70℃; for 1h;

2-n-butyl-4-chloro-1H-imidazol-5-carboxaldehyde (83857-96-9) + 1,3-chlorobromopropane (109-70-6) → 2-butyl-4-chloro-1-(3-chloropropyl)-1H-imidazole-5-carboxaldehyde (1165931-51-0)

Conditions	Yield
With potassium carbonate In acetone for 2h; Reflux;	92%
With potassium carbonate In acetone at 60℃; for 2h;	70%

5-[4'-(bromomethyl)biphenyl-2-yl]-1-(p-methoxybenzyl)-1H-tetrazole (1307853-40-2) + 2-n-butyl-4-chloro-1H-imidazol-5-carboxaldehyde (83857-96-9) → 2-butyl-4-chloro-1-({2'-[1-(p-methoxybenzyl)-1H-tetrazol-5-yl]-biphenyl-4-yl}-methyl)imidazole-5-carbaldehyde (1307853-51-5)

Conditions	Yield
With potassium carbonate In N,N-dimethyl acetamide at -10 - 20℃; for 8h;	92%

5-[4'-(bromomethyl)biphenyl-2-yl]-1-(p-methoxybenzyl)-1H-tetrazole (1307853-40-2) + 2-n-butyl-4-chloro-1H-imidazol-5-carboxaldehyde (83857-96-9) → C30H31ClN6O2

Conditions	Yield
With potassium carbonate In ISOPROPYLAMIDE at -10 - 20℃; for 8h; Inert atmosphere;	92%

p-methyloxycarbonylbenzyl chloride (34040-64-7) + 2-n-butyl-4-chloro-1H-imidazol-5-carboxaldehyde (83857-96-9) → 2-butyl-4-chloro-1-<(4-carbomethoxyphenyl)methyl>-1H-imidazole-5-carboxaldehyde (133040-02-5)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20 - 25℃; for 10h; Temperature;	91.9%

para-chloroacetophenone (99-91-2) + 2-n-butyl-4-chloro-1H-imidazol-5-carboxaldehyde (83857-96-9) → 1-(4-chlorophenyl)-3-(2-butyl-4-chloro-1H-imidazol-5-yl)-2-propen-1-one (1206796-57-7)

Conditions	Yield
With potassium hydroxide In PEG-400 at 40℃; for 1h; Claisen-Schmidt condensation;	91%
With potassium hydroxide

2-n-butyl-4-chloro-1H-imidazol-5-carboxaldehyde (83857-96-9) → 2-n-butyl-4-chloro-5-hydroxymethylimidazole (79047-41-9)

Conditions	Yield
With sodium tetrahydroborate In methanol at 20℃; for 2h;	90%
With hydrogen; magnesium In methanol at 20℃; under 258.574 - 413.718 Torr; for 0.583333h;

1-bromo-2-(bromomethyl)-4,5-dimethoxybenzene (53207-00-4) + 2-n-butyl-4-chloro-1H-imidazol-5-carboxaldehyde (83857-96-9) → 1-(2-bromo-4,5-dimethoxybenzyl)-2-butyl-4-chloro-1H-imidazole-5-carbaldehyde

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 10h;	90%

2-n-butyl-4-chloro-1H-imidazol-5-carboxaldehyde (83857-96-9) + (3,4-methylenedioxy)-6-methylbenzyl chloride (117661-72-0) → 2-butyl-4-chloro-1-(6-methyl-1,3-benzodioxol-5-ylmethyl)-1H-imidazole-5-carbaldehyde

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 10h;	90%

2-n-butyl-4-chloro-1H-imidazol-5-carboxaldehyde (83857-96-9) + 1-bromomethyl-4-bromobenzene (589-15-1) → 2-n-Butyl-4-chloro-1-p-bromobenzyl-1H-imidazole-5-carboxaldehyde (143722-29-6)

Conditions	Yield
With potassium carbonate In N,N-dimethyl acetamide; water; toluene	89.9%
With potassium carbonate In N,N-dimethyl acetamide; water; toluene	89.9%

2-n-butyl-4-chloro-1H-imidazol-5-carboxaldehyde (83857-96-9) + methyl iodide (74-88-4) → 2-butyl-4-chloro-1-methyl-1H-imidazole-5-carbaldehyde (1332222-81-7)

Conditions	Yield
Stage #1: 2-n-butyl-4-chloro-1H-imidazol-5-carboxaldehyde With sodium hydride In N,N-dimethyl-formamide at 0℃; Stage #2: methyl iodide In N,N-dimethyl-formamide at 20℃; for 4h;	89.6%
With potassium carbonate In N,N-dimethyl-formamide	89.6%

Methyl 4-(bromomethyl)benzoate (2417-72-3) + 2-n-butyl-4-chloro-1H-imidazol-5-carboxaldehyde (83857-96-9) → 2-butyl-4-chloro-1-<(4-carbomethoxyphenyl)methyl>-1H-imidazole-5-carboxaldehyde (133040-02-5)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide	89%
Stage #1: 2-n-butyl-4-chloro-1H-imidazol-5-carboxaldehyde With potassium carbonate In N,N-dimethyl-formamide at 25 - 30℃; for 0.5h; Stage #2: Methyl 4-(bromomethyl)benzoate In N,N-dimethyl-formamide at 0 - 30℃; for 19.5 - 23.5h;	82.12%
With potassium carbonate In N,N-dimethyl-formamide Alkylation;
With caesium carbonate In N,N-dimethyl-formamide
With potassium carbonate In N,N-dimethyl-formamide at 25 - 70℃; for 12.5h;

Methyl 4-(bromomethyl)benzoate (2417-72-3) + 2-n-butyl-4-chloro-1H-imidazol-5-carboxaldehyde (83857-96-9) → 2-butyl-4-chloro-1-<(4-carbomethoxyphenyl)methyl>-1H-imidazole-5-carboxaldehyde (133040-02-5) + 4-(2-Butyl-5-chloro-4-formyl-imidazol-1-ylmethyl)-benzoic acid methyl ester

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 70℃; for 1h;	A 89% B n/a
With potassium carbonate In N,N-dimethyl-formamide at 70℃; for 1h;

2-n-butyl-4-chloro-1H-imidazol-5-carboxaldehyde (83857-96-9) + 4'-bromomethyl-biphenyl-2-carboxylic acid tert-butyl ester (114772-40-6) → 4’-(2-butyl-4-chloro-5-formylimidazol-1-ylmethyl)biphenyl-2-carboxylic acid t-butyl ester (133694-34-5)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; Inert atmosphere;	89%
With potassium carbonate In N,N-dimethyl-formamide at 20℃;

4'-(bromomethyl)-3-hydroxybiphenyl-2-carbaldehyde oxime + 2-n-butyl-4-chloro-1H-imidazol-5-carboxaldehyde (83857-96-9) → 4-chloro-1-({3'-hydroxy-2'-[E-(hydroxyimino)methyl]biphenyl-4-yl}methyl)-2-butyl-5-carbaldehyde imidazole

Conditions	Yield
With potassium carbonate In N,N-dimethyl acetamide at 20℃; for 2h;	89%

N,N-didesmethylvenlafaxine (93413-77-5, 272788-06-4, 273720-73-3) + 2-n-butyl-4-chloro-1H-imidazol-5-carboxaldehyde (83857-96-9) → 2-(2-butyl-4-chloro-1H-imidazol-5-yl)-5-(4-methoxyphenyl)-1-oxa-3-azaspiro[5.5]undecane

Conditions	Yield
With potassium carbonate In methanol at 20℃; for 9h;	89%

2-n-butyl-4-chloro-1H-imidazol-5-carboxaldehyde (83857-96-9) → 2-butyl-4-chloro-1H-imidazolyl-5-methaldoxime (634907-73-6)

Conditions	Yield
With sodium acetate; hydroxylamine sulfate In methanol Heating;	88%
With sodium acetate; hydroxylamine sulfate In methanol at 60℃;

2-n-butyl-4-chloro-1H-imidazol-5-carboxaldehyde (83857-96-9) + 4'-(bromomethyl)-1,1'-biphenyl-2-carbonitrile (114772-54-2) → 2-n-Butyl-4-chloro-1-[(2'-cyanobiphenyl-4-yl)-methyl]-5-(hydroxymethyl)imidazole (114772-55-3)

Conditions	Yield
Stage #1: 2-n-butyl-4-chloro-1H-imidazol-5-carboxaldehyde; 4'-(bromomethyl)-1,1'-biphenyl-2-carbonitrile With potassium carbonate In 1-methyl-pyrrolidin-2-one at 70 - 75℃; Stage #2: With sodium tetrahydroborate In 1-methyl-pyrrolidin-2-one at 30℃; Stage #3: With water In 1-methyl-pyrrolidin-2-one; isopropyl alcohol at 75 - 80℃; for 1.5h;	88%
With tetrabutylammomium bromide; sodium hydroxide In water; toluene at 20℃;
With tetrabutylammomium bromide; water; sodium hydroxide In toluene at 20℃;

2-n-butyl-4-chloro-1H-imidazol-5-carboxaldehyde (83857-96-9) + edaravone (89-25-8) → 3-(2-butyl-4-chloro-1H-imidazol-5-yl-methylene)-4-methyl-1-phenyl-1H-pyrrol-2(3H)one (1268160-00-4)

Conditions	Yield
With sodium acetate at 60 - 80℃; for 1.33333h; Green chemistry;	88%

1-[2-amino-1-(4-methoxyphenyl)ethyl]cyclohexanol monoacetate + 2-n-butyl-4-chloro-1H-imidazol-5-carboxaldehyde (83857-96-9) → 2-(2-butyl-4-chloro-1H-imidazol-5-yl)-5-(4-methoxyphenyl)-1-oxa-3-azaspiro[5.5]undecane

Conditions	Yield
With potassium carbonate	88%

2-chloro-1-(2,4-dihydroxyphenyl)ethanone (25015-92-3) + 2-n-butyl-4-chloro-1H-imidazol-5-carboxaldehyde (83857-96-9) → 2-(2-butyl-4-chloro-1H-imidazol-5-yl)-7-hydroxy-4H-chromen-4-one

Conditions	Yield
With sodium hydroxide In ethanol; water at 20℃; for 24h;	86.3%
With sodium hydroxide In ethanol at 20℃; for 24h;	76.9%

4-bromomethylphenylboronic acid (68162-47-0) + 2-n-butyl-4-chloro-1H-imidazol-5-carboxaldehyde (83857-96-9) → (4-((2-butyl-4-chloro-5-formyl-1H-imidazol-1-yl)methyl)phenyl)-boronic acid (894806-32-7)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide for 3h;	86%

Upstream product

• 838-57-3 ETHYL 4-NITROBENZOYLACETATE 
• 83856-66-0 5,7-dihydroxy-2-(4-hydroxyphenyl)-6-[3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl]-8-(2,3,4-trihydroxypentanoyl)-4H-chromen-4-one (non-preferred name) 
• 83856-13-7 MAST CELL DEGRANULATING PEPTIDE 
• 83855-92-9 (1R,2S,3S,4R,6S)-4,6-diamino-3-{[3-deoxy-4-C-methyl-3-(methylamino)-beta-L-arabinopyranosyl]oxy}-2-hydroxycyclohexyl 2-amino-2,7-dideoxy-D-glycero-alpha-D-gluco-heptopyranoside 
• 83855-86-1 N,N-dimethyldodecan-1-amine 
• 83855-79-2 DEXTRAN HYDROXYPROPYLTRIMONIUM CHLORIDE 
• 83855-52-1 [3-[4-(ethoxycarbonylamino)phenoxy]-2-hydroxy-propyl]-tert-butyl-azani um chloride 
• 83855-51-0 Carbamic acid, (4-(2-hydroxy-3-((1-methylethyl)amino)propoxy)phenyl)-, ethyl ester, monohydrochloride 
• 83855-50-9 N-tert-butyl-3-{3-[(ethoxycarbonyl)amino]phenoxy}-2-hydroxypropan-1-aminium chloride 
• 83855-49-6 3-{3-[(ethoxycarbonyl)amino]phenoxy}-2-hydroxy-N-(propan-2-yl)propan-1-aminium chloride 
• 83855-48-5 [3-[2-(ethoxycarbonylamino)phenoxy]-2-hydroxy-propyl]-tert-butyl-azani um chloride 
• 83855-47-4 CARBAMIC ACID, (2-(2-HYDROXY-3-((1-METHYLETHYL)AMINO)PROPOXY)PHENYL)-, ETHYL EST 
• 83855-40-7 Antibiotic an 5 
• 838-55-1 N-(2-Chlorophenyl)-4-fluorobenzaMide, 97% 

Downstream Products

• 83858-04-2 4-Pyrimidinecarbonitrile,2-phenyl-(9CI) 
• 83858-06-4 6-PHENYLPYRIMIDINE-4-CARBONITRILE 
• 83858-07-5 2-Dimethylamino-4-(4-fluorophenyl)pyrimidine 
• 83858-82-6 Piperazinomycin 
• 838-59-5 DI(ALPHA-PHENYLETHYL) SULFIDE 
• 83859-88-5 4-aminobenzenediazonium ouabain 
• 83860-24-6 12-hydroxymethylretinoic acid delta-lactone 
• 83860-29-1 (tolylazo)toluidinium chloride 
• 83860-31-5 alpha-cyano-3-phenoxybenzyl [1S-[1alpha(R*),3beta]]-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate 
• 83860-32-6 alpha-cyano-3-phenoxybenzyl [1S-[1alpha(S*),3beta]]-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate 
• 83860-41-7 2-amino-N-[4-amino-3-[3-amino-6-(ethylaminomethyl)oxan-2-yl]oxy-2-hydr oxy-6-methoxy-cyclohexyl]-N-methyl-acetamide, carbonic acid 
• 83860-42-8 Istamycin C(sub 0) 
• 83860-51-9 4'-Propyl-[1,1'-bicyclohexyl]-4-carboxylic acid 
• 838605-73-5 N-benzyl-4-bromo-3-ethoxybenzenesulfonamide 

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