4'-Mercaptoacetanilide → N-{4-[2-(5,6-Dichloro-1-methyl-1H-benzoimidazol-2-yl)-2-hydroxy-propylsulfanyl]-phenyl}-acetamide

HRID 2043248Notes

Reaction equation

HRID 2043248 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].[C:18]([NH:21][C:22]1[CH:27]=[CH:26][C:25]([SH:28])=[CH:24][CH:23]=1)(=[O: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:28][C:25]3[CH:24]=[CH:23][C:22]([NH:21][C:18](=[O:20])[CH3:19])=[CH:27][CH:26]=3)=[N:7][C:8]=2[CH:15]=1

Participants

5

Reactant 3

HCID 707774'-MercaptoacetanilideHCID 10942334Sodium MethoxideHCID 116522571-Chloro-2-(5,6-dichloro-1-methyl-1H-benzoimidazol-2-yl)-propan-2-ol

Product 1

HCID 59682308N-{4-[2-(5,6-Dichloro-1-methyl-1H-benzoimidazol-2-yl)-2-hydroxy-propylsulfanyl]-phenyl}-acetamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 1-chloro-2-(5,6-dichloro-1-methyl-1H-benzoimidazol-2-yl)-propan-2-ol (60 mg) in MeOH (2 mL) at room temperature was added a solution of 4-acetamidothiophenol (40 mg) and sodium methoxide (0.047 mls of 25 wt % in MeOH). The resulting mixture was stirred at room temperature overnight. The reaction mixture was concentrated. The crude product was purified by flash chromatography (25%-100% EtOAc/hexanes) to yield the title compound as a white foam solid.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customThe crude product was purified by flash chromatography (25%-100% EtOAc/hexanes)

Sources & evidence

ORD record
ord-4ae529c934534261a172c848f8478b7b
Source dataset
uspto-grants-2013_11
Patent number
US08586616B2

Reaction notes

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