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

HRID 230395Notes

Reaction equation

HRID 230395 reaction equation
Cl[CH2:2][C:3]([C:6]1[N:10]([CH2:11][CH3:12])[C:9]2[CH:13]=[C:14]([Cl:18])[C:15]([Cl:17])=[CH:16][C:8]=2[N:7]=1)([OH:5])[CH3:4].[CH2:19]([SH:21])[CH3:20].C[O-].[Na+]>CO>[Cl:17][C:15]1[C:14]([Cl:18])=[CH:13][C:9]2[N:10]([CH2:11][CH3:12])[C:6]([C:3]([OH:5])([CH3:4])[CH2:2][S:21][CH2:19][CH3:20])=[N:7][C:8]=2[CH:16]=1

Participants

5

Reactant 3

HCID 6343EthanethiolHCID 10942334Sodium MethoxideHCID 66968899HCID 66968899, compound

Product 1

HCID 116599942-(5,6-Dichloro-1-ethyl-1H-benzoimidazol-2-yl)-1-ethylsulfanyl-propan-2-ol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 1-chloro-2-(5,6-dichloro-1-ethyl-1H-benzoimidazol-2-yl)-propan-2-ol (161 mg) in methanol (5 mL) at room temperature was added a solution of ethanethiol (37 mg) and sodium methoxide (0.144 mls of 25 wt % in MeOH). The resulting mixture was stirred at room temperature overnight. The reaction mixture was quenched with NH4Cl (aq), extracted with EtOAc, and dried over Na2SO4. The crude product was purified by flash chromatography (10%-40% EtOAc/hexanes) to yield the title compound as an off-white solid.

Workup

  1. customThe reaction mixture was quenched with NH4Cl (aq)
  2. extractionextracted with EtOAc
  3. dry with materialdried over Na2SO4
  4. customThe crude product was purified by flash chromatography (10%-40% EtOAc/hexanes)

Sources & evidence

ORD record
ord-9a4142a8f1044e7cac8624f5f8ccbe1c
Source dataset
uspto-grants-2009_07
Patent number
US07566733B2

Reaction notes

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