Water → HCID 22316751, compound

HRID 396769Notes

Reaction equation

HRID 396769 reaction equation
[F:1][CH2:2][S:3]([C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[CH:8][CH:7]=1)(=[O:5])=[O:4].[NH2:13][NH2:14].O.Cl.CO>CN(C=O)C>[ClH:12].[F:1][CH2:2][S:3]([C:6]1[CH:11]=[CH:10][C:9]([NH:13][NH2:14])=[CH:8][CH:7]=1)(=[O:5])=[O:4]

Participants

6

Reactant 4

HCID 962WaterHCID 9321HydrazineHCID 21893726Hydrochloride methanolHCID 22316655HCID 22316655, compound

Product 1

HCID 22316751HCID 22316751, compoundYield 49.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-chlorophenyl fluoromethyl sulfone (1.97 g, 9.44 mmol. prepared according to the method of Ukrainskill Khimicheskill Zhurnal, 1972, 38. 1034) and hydrazine anhydrous (1.84 g, 57.5 mmol) in DMF (30 mL) was heated to 120° C. for 16 hours, and cooled down to room temperature. The reaction mixture was poured into water (150 mL) and the whole was extracted with ethyl acetate/hexane/ether (2/1/1, 60 mL×3). The organic layer was washed with brine, dried over sodium sulfate, and concentrated in vacuo. The resulting solid (1.56 g, 7.64 mmol) was added HCl-MeOH reagent 10 (10 mL) at room temperature and stirred for 10 minutes. The mixture was concentrated in vacuo to give the subtitle compound (0.91 g, 49.4% yield).

Workup

  1. customprepared
  2. extractionthe whole was extracted with ethyl acetate/hexane/ether (2/1/1, 60 mL×3)
  3. washThe organic layer was washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. concentrationThe mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-f9c2e37fb5d24c36a23ff17e75857d14
Source dataset
uspto-grants-2003_08
Patent number
US06608095B2

Reaction notes

Loading…