Water → HCID 54470532, compound

HRID 1719226Notes

Reaction equation

HRID 1719226 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[N:11][OH:12])[C:9]#[N:10])=[CH:4][CH:3]=1.[C:13]1([CH3:23])[CH:18]=[CH:17][C:16]([S:19](Cl)(=[O:21])=[O:20])=[CH:15][CH:14]=1.O>N1C=CC=CC=1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8](=[N:11][O:12][S:19]([C:16]2[CH:17]=[CH:18][C:13]([CH3:23])=[CH:14][CH:15]=2)(=[O:21])=[O:20])[C:9]#[N:10])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 73183931HCID 73183931, compound

Product 1

HCID 54470532HCID 54470532, compoundYield 93.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A stirred solution of 2-(4-fluorophenyl)-2-hydroxyiminoacetonitrile (42.8 g, 0.26 mole) in 200 ml of pyridine was cooled to 0° C., and p-toluenesulfonyl chloride (76.0 g, 0.39 mole) was added portionwise. Upon complete addition, the reaction mixture was stirred at 0°-5° C. for one hour and then stored in a refrigerator for 16 hours. The resultant slurry was poured into a mixture of ice and water and stirred for 30 minutes. The mixture was then filtered and the white filter cake dried under vacuum without heat to give 2-(4-fluorophenyl)-2-(4-methylphenylsulfonyloxy)iminoacetonitrile (77.3 g, mp 129°-140° C.).

Workup

  1. additionUpon complete addition
  2. waitstored in a refrigerator for 16 hours
  3. stirringstirred for 30 minutes
  4. filtrationThe mixture was then filtered
  5. customthe white filter cake dried under vacuum
  6. temperaturewithout heat

Sources & evidence

ORD record
ord-b4e6a278cae947c9a812a8762b06e48e
Source dataset
uspto-grants-1985_09
Patent number
US04539328

Reaction notes

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