Phosphorus oxychloride → HCID 178527270, compound

HRID 496261Notes

Reaction equation

HRID 496261 reaction equation
[F:1][C:2]([F:17])([F:16])[S:3]([C:6]1[CH:15]=[CH:14][C:9]2[NH:10][C:11](=O)[NH:12][C:8]=2[CH:7]=1)(=[O:5])=[O:4].O=P(Cl)(Cl)[Cl:20]>>[Cl:20][C:11]1[NH:10][C:9]2[CH:14]=[CH:15][C:6]([S:3]([C:2]([F:17])([F:16])[F:1])(=[O:5])=[O:4])=[CH:7][C:8]=2[N:12]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 15484057HCID 15484057, compound

Product 1

HCID 178527270HCID 178527270, compound

Procedure

Reflux 5-trifluoromethylsulfonyl-1,3-dihydro-benzimidazol-2-one (380 mg) for 8 hours in POCl3 (10 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-trifluoromethylsulfonyl-1H-benzimidazole. G. 1′-(5-trifluoromethylsulfonyl-1H-benzimidazol-2-yl)-spiro[isobenzofuran-1,4′-piperidin]-3-one

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-8ba7dd3e7f9b4a4cb98a9ffc6d9a4d6a
Source dataset
uspto-grants-2005_09
Patent number
US06943199B2

Reaction notes

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