Sodium Bicarbonate → Methyl 7-Methoxy-2-phenyl-1H-benzo[d]imidazole-4-carboxylate

HRID 349468

Reaction equation

HRID 349468 reaction equation
[CH3:1][O:2][C:3](=[O:22])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[C:6]([NH:12][C:13](=[N:20]Cl)[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:5]=1.C([O-])(O)=O.[Na+]>CO>[CH3:1][O:2][C:3]([C:4]1[C:5]2[N:20]=[C:13]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[NH:12][C:6]=2[C:7]([O:10][CH3:11])=[CH:8][CH:9]=1)=[O:22]

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 691195744-methoxy-3-[(N-chloro-benzimidoyl)-amino]-benzoic acid methyl ester

Product 1

HCID 22663468Methyl 7-Methoxy-2-phenyl-1H-benzo[d]imidazole-4-carboxylateYield 86%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4-methoxy-3-[(N-chloro-benzimidoyl)-amino]-benzoic acid methyl ester (8 g, 25.10 mmol) obtained in step 1 was dissolved in 50 ml of 50% methanol and NaHCO3 (5.32 g, 50.20 mmol) was added dropwise thereto at room temperature and refluxed for 5 min. The resulting solution was cooled to room temperature, extracted with ethyl acetate, and the extract was concentrated under a reduced pressure. The resulting residue was purified by recrystallization from ethyl acetate/hexane to obtain the title compound (6 g, 15.94 mmol) in a yield of 86%.

Workup

  1. temperatureThe resulting solution was cooled to room temperature
  2. extractionextracted with ethyl acetate
  3. concentrationthe extract was concentrated under a reduced pressure
  4. customThe resulting residue was purified by recrystallization from ethyl acetate/hexane

Sources & evidence

ORD record
ord-101a51ed302b45698fe40ee685a36982
Source dataset
uspto-grants-2007_02
Patent number
US07179832B2

Linked notes

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