Isobutyl mercaptan → 2-(5,6-Dichloro-1-methyl-1H-benzoimidazol-2-yl)-1-isobutylsulfanyl-propan-2-ol

HRID 230397Notes

Reaction equation

HRID 230397 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].[CH3:18][CH:19]([CH3:22])[CH2:20][SH:21].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:21][CH2:20][CH:19]([CH3:22])[CH3:18])=[N:7][C:8]=2[CH:15]=1

Participants

5

Reactant 3

HCID 10558Isobutyl mercaptanHCID 10942334Sodium MethoxideHCID 116522571-Chloro-2-(5,6-dichloro-1-methyl-1H-benzoimidazol-2-yl)-propan-2-ol

Product 1

HCID 444395342-(5,6-Dichloro-1-methyl-1H-benzoimidazol-2-yl)-1-isobutylsulfanyl-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 (408 mg) in methanol (10 mL) at room temperature was added a solution of 2-methyl-1-propanethiol (150 mg) and sodium methoxide (0.381 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 light orange 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-3cab78068da7455ab9d65f848702f115
Source dataset
uspto-grants-2009_07
Patent number
US07566733B2

Reaction notes

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