Ethyl bromoacetate → ethyl [(5-methoxy-1H-benzimidazol-2-yl)sulfanyl]acetate

HRID 579463

Reaction equation

HRID 579463 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[N:10]=[C:9]([SH:11])[NH:8][C:7]=2[CH:12]=1.[H-].[Na+].[CH2:15]([O:17][C:18](=[O:21])[CH2:19]Br)[CH3:16]>CN(C=O)C>[CH2:15]([O:17][C:18](=[O:21])[CH2:19][S:11][C:9]1[NH:8][C:7]2[CH:12]=[C:3]([O:2][CH3:1])[CH:4]=[CH:5][C:6]=2[N:10]=1)[CH3:16]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 178488032HCID 178488032, compound

Product 1

HCID 871011ethyl [(5-methoxy-1H-benzimidazol-2-yl)sulfanyl]acetateYield 99.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6-Methoxy-1H-benzoimidazole-2-thiol (10.00 g, 55.56 mmol) was dissolved in DMF (300 mL). NaH (2.44 g, 60 w/w % in mineral oil, 61.11 mmol) was added in small portions at room temperature. The resulted mixture was stirred for one h then bromo-acetic acid ethyl ester (10.21 g, 61.11 mmol) was added. After 12 h the mixture was evaporated and the resulted slurry was diluted with HCl (340 mL, 2N) and was stirred for a 0.5 h at room temperature then was filtered, washed with water and n-hexane respectively. The title compound (14.70 g, 99%) was isolated as a pale yellow powder.

Workup

  1. customAfter 12 h the mixture was evaporated
  2. additionthe resulted slurry was diluted with HCl (340 mL, 2N)
  3. stirringwas stirred for a 0.5 h at room temperature
  4. filtrationthen was filtered
  5. washwashed with water and n-hexane respectively

Sources & evidence

ORD record
ord-f8ca09fdd2c64e948577eda2feb0fcad
Source dataset
uspto-grants-2015_05
Patent number
US09040714B2

Linked notes

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