Phosphorus oxychloride → HCID 178527270, compound

HRID 413245Notes

Reaction equation

HRID 413245 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.

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-a51041e9b2da4d7887a080aeb80a2f92
Source dataset
uspto-grants-2003_05
Patent number
US06566367B2

Reaction notes

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