Propargyl bromide → 1-Phenyl-1-propynyl-2-(3-sulphamoyl-4-chlorobenzoyl)-hydrazine

HRID 127967Notes

Reaction equation

HRID 127967 reaction equation
[C:1]1([NH:7][NH:8][C:9](=[O:21])[C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[C:12]([S:17](=[O:20])(=[O:19])[NH2:18])[CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:22](Br)[C:23]#[CH:24]>CN(C)C=O>[C:1]1([N:7]([C:22]#[C:23][CH3:24])[NH:8][C:9](=[O:21])[C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[C:12]([S:17](=[O:20])(=[O:19])[NH2:18])[CH:11]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 7842Propargyl bromideHCID 155715011-Phenyl-2-(3-sulfamoyl-4-chlorobenzoyl)-hydrazine

Product 1

HCID 234710111-Phenyl-1-propynyl-2-(3-sulphamoyl-4-chlorobenzoyl)-hydrazine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-Phenyl-2-(3-sulfamoyl-4-chlorobenzoyl)-hydrazine 5 g (0.015 mol) was dissolved in dimethylformamide (20 ml). To this was added propargyl bromide 3.6 g (0.03 mol) and the mixture heated at 95°-100° C. for about 2 hours. The reaction mixture was concentrated under reduced pressure at about 40°-45° C. on a rotary evaporator. The concentrate was then diluted with approximately 2 volumes of isopropanol and added slowly to about 600 ml of vigorously stirred water. The precipitate was collected by filtration, washed with water and dried under reduced pressure to provide 1-phenyl-1-propynyl-2-(3-sulphamoyl-4-chlorobenzoyl)-hydrazine (m.p. 168°-170° C.).

Workup

  1. temperaturethe mixture heated at 95°-100° C. for about 2 hours
  2. concentrationThe reaction mixture was concentrated under reduced pressure at about 40°-45° C. on a rotary evaporator
  3. additionThe concentrate was then diluted with approximately 2 volumes of isopropanol
  4. additionadded slowly to about 600 ml of vigorously stirred water
  5. filtrationThe precipitate was collected by filtration
  6. washwashed with water
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-bc89eb0d2df646f996f9f6665bf9d40e
Source dataset
uspto-grants-1981_03
Patent number
US04258059

Reaction notes

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