Water → HCID 13798286, compound

HRID 580255Notes

Reaction equation

HRID 580255 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([O:9][S:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)(=[O:12])=[O:11])=[CH:4][C:3]=1[NH:19][NH2:20].O.[C:22]1([CH3:28])[CH:27]=[CH:26]C=[CH:24][CH:23]=1>>[F:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([O:9][S:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)(=[O:12])=[O:11])=[CH:4][C:3]=1[N:19]1[C:27]([CH3:26])=[C:22]([CH3:28])[C:23]([CH3:24])=[N:20]1

Participants

4

Reactant 3

HCID 962WaterHCID 1140TolueneHCID 20134634HCID 20134634, compound

Product 1

HCID 13798286HCID 13798286, compound

Conditions

Temperature
70 °C

Procedure

A mixture of (2-fluoro-4-chloro-5-phenylsulfonyloxyphenyl)-hydrazine (31.7 g), 3-methylpenta-2,4-dione (11.4 g) and water (150 ml) was stirred at 70° C. for one hour. After the reaction mixture was cooled, toluene was added thereto whereby to form two layers. The toluene layer thus separated was washed with water and dried over anhydrous sodium sulfate. Removal of the solvent by distillation in vacuo gave the titled compound (37.5 g) as a pale brown crystalline solid. Recrystallization of this solid from carbon tetrachloride afforded a white crystalline solid. nD23 =1.5492.

Workup

  1. temperatureAfter the reaction mixture was cooled
  2. customwhereby to form two layers
  3. customThe toluene layer thus separated
  4. washwas washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. customRemoval of the solvent
  7. distillationby distillation in vacuo

Sources & evidence

ORD record
ord-d0ec56ebac41495ab17e9644566c7ff7
Source dataset
uspto-grants-1988_06
Patent number
US04752326

Reaction notes

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