Water → HCID 19707996, compound

HRID 724782Notes

Reaction equation

HRID 724782 reaction equation
[F:1][C:2]([F:18])([F:17])[O:3][C:4]1[CH:5]=[C:6]([N:10]2[CH2:14][CH2:13][CH:12]([OH:15])[C:11]2=[O:16])[CH:7]=[CH:8][CH:9]=1.C(N(CC)CC)C.[CH3:26][S:27](Cl)(=[O:29])=[O:28].O>ClCCl>[F:18][C:2]([F:1])([F:17])[O:3][C:4]1[CH:5]=[C:6]([N:10]2[CH2:14][CH2:13][CH:12]([O:15][S:27]([CH3:26])(=[O:29])=[O:28])[C:11]2=[O:16])[CH:7]=[CH:8][CH:9]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471Triethylamine2×HCID 31297Methanesulfonyl chloride2×HCID 19707995HCID 19707995, compound

Product 1

HCID 19707996HCID 19707996, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A stirred solution of 1-(3-trifluoromethoxyphenyl)-3-hydroxy-2-pyrrolidone (19.42 g) in dichloromethane (250 ml) was cooled in an ice bath and treated with triethylamine (11.32 ml). Methanesulfonyl chloride (6.05 ml) was added dropwise via a syringe, and the mixture stirred with cooling for a further 1 hour after which it was allowed to warm to room temperature. After stirring for 2 hours at room temperature methanesulfonyl chloride (0.5 ml) and triethylamine (1.0 ml) were added and the mixture was stirred for a further 2 hours. The reaction mixture was poured into water and extracted with dichloromethane. The dichloromethane extracts were washed with water, dried (MgSO4) and the solvent evaporated under reduced pressure to give the crude sub-title compound (23.0 g), which was used without further purification.

Workup

  1. temperaturewith cooling for a further 1 hour after which it
  2. additionwere added
  3. stirringthe mixture was stirred for a further 2 hours
  4. extractionextracted with dichloromethane
  5. washThe dichloromethane extracts were washed with water
  6. dry with materialdried (MgSO4)
  7. customthe solvent evaporated under reduced pressure

Sources & evidence

ORD record
ord-c55ed7a6c86041acb4c080ef8f44d9b4
Source dataset
uspto-grants-1998_01
Patent number
US05705456

Reaction notes

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