Ethanethiol → 2-(5,6-Dichloro-1-methyl-1H-benzoimidazol-2-yl)-1-ethylsulfanyl-propan-2-ol

HRID 230398Notes

Reaction equation

HRID 230398 reaction equation
Cl[CH2:2][C:3]([C:6]1[N:10]([CH3:11])[C:9]2[CH:12]=[C:13]([Cl:17])[C:14]([Cl:16])=[CH:15][C:8]=2[N:7]=1)([OH:5])[CH3:4].[CH2:18]([SH:20])[CH3:19].C[O-].[Na+]>CO>[Cl:16][C:14]1[C:13]([Cl:17])=[CH:12][C:9]2[N:10]([CH3:11])[C:6]([C:3]([OH:5])([CH3:4])[CH2:2][S:20][CH2:18][CH3:19])=[N:7][C:8]=2[CH:15]=1

Participants

5

Reactant 3

HCID 6343EthanethiolHCID 10942334Sodium MethoxideHCID 116522571-Chloro-2-(5,6-dichloro-1-methyl-1H-benzoimidazol-2-yl)-propan-2-ol

Product 1

HCID 116238782-(5,6-Dichloro-1-methyl-1H-benzoimidazol-2-yl)-1-ethylsulfanyl-propan-2-ol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 1-chloro-2-(5,6-dichloro-1-methyl-1H-benzoimidazol-2-yl)-propan-2-ol (141 mg) in MeOH (4 mL) at room temperature was added a solution of ethanethiol (34 mg) and sodium methoxide (0.132 mls of 25 wt % in MeOH). The resulting mixture was stirred at room temperature overnight. The reaction mixture was then concentrated. The crude product was purified by flash chromatography (10%-40% EtOAc/hexanes) to yield the title compound as a yellow crystalline solid.

Workup

  1. concentrationThe reaction mixture was then concentrated
  2. customThe crude product was purified by flash chromatography (10%-40% EtOAc/hexanes)

Sources & evidence

ORD record
ord-d42359d6f16d4e1c820b60b9ed7cae3a
Source dataset
uspto-grants-2009_07
Patent number
US07566733B2

Reaction notes

Loading…