Water → 2-((5,6-Dimethyl-1-(phenylcarbonyl)benzimidazole-2-ylthio)methyl)benzoic acid t-butyl ester

HRID 916080Notes

Reaction equation

HRID 916080 reaction equation
[C:1]([O:5][C:6](=[O:26])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[CH2:13][S:14][C:15]1[NH:16][C:17]2[CH:23]=[C:22]([CH3:24])[C:21]([CH3:25])=[CH:20][C:18]=2[N:19]=1)([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[C:34](Cl)(=[O:41])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.O>C(Cl)(Cl)Cl>[C:1]([O:5][C:6](=[O:26])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[CH2:13][S:14][C:15]1[N:16]([C:34]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)=[O:41])[C:17]2[CH:23]=[C:22]([CH3:24])[C:21]([CH3:25])=[CH:20][C:18]=2[N:19]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 694570282-((5,6-Dimethylbenzimidazole-2-ylthio)methyl)benzoic acid t-butyl ester

Product 1

HCID 694582302-((5,6-Dimethyl-1-(phenylcarbonyl)benzimidazole-2-ylthio)methyl)benzoic acid t-butyl ester

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

2-((5,6-dimethylbenzimidazole-2-ylthio)methyl)benzoic acid t-butyl ester (30 mg, 0.082 mmol) was dissolved in 3 ml of chloroform, to which triethylamine (17 μl, 0.123 mmol) and benzoyl chloride (14 μl, 0.123 mmol) were sequentially added and the mixture was stirred at room temperature for 2 hours. After the reaction was complete, water was added, followed by extraction with ethyl acetate. After drying the ethyl acetate phase with anhydrous sodium sulfate, it was concentrated, and 2-((5,6-dimethyl-1-(phenylcarbonyl)benzimidazole-2-ylthio)methyl)benzoic acid t-butyl ester was obtained (38 mg, yield quantitative).

Workup

  1. additionwere sequentially added
  2. extractionfollowed by extraction with ethyl acetate
  3. dry with materialAfter drying the ethyl acetate phase with anhydrous sodium sulfate, it
  4. concentrationwas concentrated

Sources & evidence

ORD record
ord-ad49f7b84bbc4d8d9dbf4150bf890d56
Source dataset
uspto-grants-2007_09
Patent number
US07268145B2

Reaction notes

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