Hydrochloric Acid → HCID 57182351, compound

HRID 1276889Notes

Reaction equation

HRID 1276889 reaction equation
[N+:1]([C:4]1[CH:14]=[CH:13][C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][C:5]=1[NH:15][C:16](=[O:24])[CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)([O-:3])=[O:2].[H-].[Na+].[CH3:27]I.Cl>CN(C)C=O>[N+:1]([C:4]1[CH:14]=[CH:13][C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][C:5]=1[N:15]([C:16](=[O:24])[CH2:17][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)[CH3:27])([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 54328965HCID 54328965, compound

Product 1

HCID 57182351HCID 57182351, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 0.924 g of ethyl 4-nitro-3-phenylacetylaminobenzoate in 10 ml of N,N-dimethylformamide were added 0.166 g of 60% sodium hydride while being cooled with ice, and the mixture was stirred at room temperature for 1 hour. Methyl iodide (0.50 ml) was added thereto, and the resulting mixture was stirred at room temperature for 1 hour. The reaction solution was poured into cold 1-N hydrochloric acid, and the mixture was extracted twice with ethyl acetate. The organic layer was washed with 1-N hydrochloric acid and then with water, and was dried. The solvent was distilled off under reduced pressure. The residue was purified through silica-gel column chromatography (developing eluent: a mixture of ethyl acetate and hexane at a ratio of from 1:10 to 1:4) to obtain 0.510 g of ethyl 4-nitro-3-[N-(methyl)phenylacetylamino]benzoate. To 0.148 g of this compound were added 2 ml of ethanol, 1 ml of acetic acid and 0.240 g of reduced iron, and the mixture was refluxed for 2 hours. The solid material was separated through filtration. The filtrate was concentrated, and was then purified through preparative thin-layer silica-gel chromatography (eluent: a mixture of chloroform and ethyl acetate at a ratio of 2:1) to give 0.090 g of 2-benzyl-6-ethoxycarbonyl-1-methylbenzimidazole (115).

Workup

  1. temperaturewhile being cooled with ice
  2. stirringthe resulting mixture was stirred at room temperature for 1 hour
  3. extractionthe mixture was extracted twice with ethyl acetate
  4. washThe organic layer was washed with 1-N hydrochloric acid
  5. dry with materialwith water, and was dried
  6. distillationThe solvent was distilled off under reduced pressure
  7. customThe residue was purified through silica-gel column chromatography (
  8. additiona mixture of ethyl acetate and hexane at a ratio of from 1:10 to 1:4)

Sources & evidence

ORD record
ord-cfbd0b1ae63c411f80440fc2a7f7f0bf
Source dataset
uspto-grants-2000_12
Patent number
US06166219

Reaction notes

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