Thionyl Chloride → 2-Chloro-1-methyl-5-nitro-1H-benzimidazole

HRID 1391544Notes

Reaction equation

HRID 1391544 reaction equation
[CH3:1][N:2]1[C:6]2[CH:7]=[CH:8][C:9]([N+:11]([O-:13])=[O:12])=[CH:10][C:5]=2[NH:4][C:3]1=S.O=S(Cl)[Cl:17]>>[Cl:17][C:3]1[N:2]([CH3:1])[C:6]2[CH:7]=[CH:8][C:9]([N+:11]([O-:13])=[O:12])=[CH:10][C:5]=2[N:4]=1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 21226931HCID 21226931, compound

Product 1

HCID 108223912-Chloro-1-methyl-5-nitro-1H-benzimidazole

Procedure

The compound 1-Methyl-5-nitro-1,3-dihydro-benzoimidazole-2-thione (5.8 g, 27.9 mmol) was heated to reflux with SOCl2 (30 ml) overnight. The reaction mixture was cooled to room temperature and poured into 300 ml of ice water and extracted with CH2Cl2. The organic layers was washed with 10% NaHCO3 water solution, brine, dried over Na2SO4 and concentrated to give the title compound as a yellow solid. MS (ESI) m/z=212 [M+H].

Workup

  1. extractionextracted with CH2Cl2
  2. washThe organic layers was washed with 10% NaHCO3 water solution, brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-95436be09f304e759035941098a0666d
Source dataset
uspto-grants-2008_03
Patent number
US07338959B2

Reaction notes

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