Water → HCID 22316751, compound

HRID 497200Notes

Reaction equation

HRID 497200 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

Conditions

Temperature
120 °C

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). MS (EI): m/z 204 (M+)

Workup

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

Sources & evidence

ORD record
ord-f871a45c08544a2eae96b875546d1cd1
Source dataset
uspto-grants-2005_09
Patent number
US06949536B2

Reaction notes

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