Isopropanol → 1-n-Propyl-1-phenyl-2-(3-sulfamoyl-4 chlorobenzoyl) hydrazine

HRID 127959

Reaction equation

HRID 127959 reaction equation
[C:1]1([N:7]([CH2:9][CH2:10][CH3:11])[NH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)(O)[O-].[Na+].C(O)(C)C.[S:21]([C:25]1[CH:26]=[C:27]([CH:31]=[CH:32][C:33]=1[Cl:34])[C:28](Cl)=[O:29])(=[O:24])(=[O:23])[NH2:22]>O>[CH2:9]([N:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[NH:8][C:28](=[O:29])[C:27]1[CH:31]=[CH:32][C:33]([Cl:34])=[C:25]([S:21](=[O:23])(=[O:24])[NH2:22])[CH:26]=1)[CH2:10][CH3:11]

Participants

6

Reactant 4

HCID 3776IsopropanolHCID 516892Sodium BicarbonateHCID 30179793-(Aminosulfonyl)-4-chlorobenzoyl chlorideHCID 123271621-Phenyl-1-propylhydrazine

Product 1

HCID 155714991-n-Propyl-1-phenyl-2-(3-sulfamoyl-4 chlorobenzoyl) hydrazine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A vigorously stirred mixture of 14.0 g (0.1 mol) 1-phenyl-1-n-propylhydrazine, 8.4 g (0.1 mol) sodium bicarbonate, and 100 ml isopropanol was chilled to 0°-5° C., 23 g (0.09 mol) 3-sulfamoyl-4-chlorobenzoyl chloride was added in one portion, and the reaction mixture was allowed to stir for several hours, gradually warming to room temperature. Dilution with water and refrigeration overnight yielded solid material which was collected and recrystallized from acetone/water, mp. 102° C. (d).

Workup

  1. temperaturewas chilled to 0°-5° C.
  2. customwas collected
  3. customrecrystallized from acetone/water, mp. 102° C. (d)

Sources & evidence

ORD record
ord-5ad3a84d3190480f938908c1fad147db
Source dataset
uspto-grants-1981_03
Patent number
US04258059

Linked notes

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