Phosphorus oxychloride → HCID 178506089, compound

HRID 413240

Reaction equation

HRID 413240 reaction equation
[F:1][C:2]([F:14])([F:13])[C:3]1[CH:12]=[CH:11][C:6]2[NH:7][C:8](=O)[NH:9][C:5]=2[CH:4]=1.O=P(Cl)(Cl)[Cl:17]>>[Cl:17][C:8]1[NH:7][C:6]2[CH:11]=[CH:12][C:3]([C:2]([F:14])([F:13])[F:1])=[CH:4][C:5]=2[N:9]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 118201505-Trifluoromethyl-1,3-dihydro-benzimidazol-2-one

Product 1

HCID 178506089HCID 178506089, compound

Procedure

Reflux 5-trifluoromethyl-1,3-dihydro-benzimidazol-2-one (17 g; Meanwell et al. (1995) J. Org. Chem. 60(6):1565-1582) for 14 hours in POCl3 (200 mL). Evaporate the solvent in vacuo, then carefully neutralize with saturated NaHCO3, and extract with EtOAc. Dry over Na2SO4, concentrate under vacuum, and purify by flash chromatography (1 :1 hexanes/EtOAc) to obtain 2-chloro-5-trifluoromethyl-1H-benzimidazole.

Workup

  1. customEvaporate the solvent in vacuo
  2. extractionextract with EtOAc
  3. dry with materialDry over Na2SO4
  4. concentrationconcentrate under vacuum
  5. custompurify by flash chromatography (1 :1 hexanes/EtOAc)

Sources & evidence

ORD record
ord-fbeaed5d9688447db1d8c343a4d15b84
Source dataset
uspto-grants-2003_05
Patent number
US06566367B2

Linked notes

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