Water → 1-Crotyl-1-phenyl-2-(3-sulfamoyl-4-chlorobenzoyl) hydrazine

HRID 1589423Notes

Reaction equation

HRID 1589423 reaction equation
CN(C)C=O.[NH2:6][S:7]([C:10]1[CH:11]=[C:12]([CH:17]=[CH:18][C:19]=1[Cl:20])[C:13]([NH:15][NH2:16])=[O:14])(=[O:9])=[O:8].[CH2:21](Br)[CH:22]=[CH:23][CH3:24].O>C(O)(C)C>[CH2:21]([N:16]([C:10]1[CH:11]=[CH:12][CH:17]=[CH:18][CH:19]=1)[NH:15][C:13](=[O:14])[C:12]1[CH:17]=[CH:18][C:19]([Cl:20])=[C:10]([S:7](=[O:9])(=[O:8])[NH2:6])[CH:11]=1)[CH:22]=[CH:23][CH3:24]

Participants

6

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 1224142-Butene, 1-bromo-HCID 24026562-Chloro-5-(hydrazinecarbonyl)benzene-1-sulfonamide

Product 1

HCID 543987431-Crotyl-1-phenyl-2-(3-sulfamoyl-4-chlorobenzoyl) hydrazine

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

In a 250 ml round bottomed flask is placed 90 ml of N,N-dimethylformamide and 30 grams (0.092 mole) of 3-amino sulfonyl-4-chlorobenzhydrazide. The mixture was stirred to dissolve the solid, then 18.63 gms (0.138 mole) of crotyl bromide were added. The mixture was heated at 100° for 1.66 hours at which point TLC showed the reaction to be complete. The reaction mixture was cooled and diluted with 200 ml isopropanol. This solution was dripped into a slurry of 1.5 liters of ice and 4 liters of water. The solid which precipitated was collected, washed with water and air dried overnight, yielding the product which could be recrystallized from chloroform/carbon tetrachloride.

Workup

  1. customIn a 250 ml round bottomed flask is placed
  2. dissolutionto dissolve the solid
  3. temperatureThe mixture was heated at 100° for 1.66 hours at which point TLC
  4. customthe reaction
  5. temperatureThe reaction mixture was cooled
  6. customThe solid which precipitated
  7. customwas collected
  8. washwashed with water and air
  9. customdried overnight
  10. customyielding the product which
  11. customcould be recrystallized from chloroform/carbon tetrachloride

Sources & evidence

ORD record
ord-c11cec87eff8428ba8b5fb41d79e3902
Source dataset
uspto-grants-1986_02
Patent number
US04570001

Reaction notes

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