Phosphorus oxychloride → HCID 178506089, compound

HRID 496256

Reaction equation

HRID 496256 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. B. 1′-(5-Trifluoromethyl-1H-benzimidazol-2-yl)-spiro[isobenzofuran-1,4′-piperidin]-3-one hydrochloride

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-71967602e6af4430b1cc7bd91ac17548
Source dataset
uspto-grants-2005_09
Patent number
US06943199B2

Linked notes

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