Triethylamine → N'-t-butyl-N-(1,2,2-trichlorovinyl)carbonyl-N'-benzoylhydrazine

HRID 849765Notes

Reaction equation

HRID 849765 reaction equation
[C:1]([N:5]([C:7](=[O:14])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[NH2:6])([CH3:4])([CH3:3])[CH3:2].[Cl:15][C:16](=[C:20]([Cl:22])[Cl:21])[C:17](Cl)=[O:18].C(N(CC)CC)C>C(Cl)Cl>[C:1]([N:5]([C:7](=[O:14])[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[NH:6][C:17]([C:16]([Cl:15])=[C:20]([Cl:22])[Cl:21])=[O:18])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 131532,3,3-Trichloro-2-propenoyl chlorideHCID 1275961N-(tert-butyl)benzohydrazide

Product 1

HCID 15294614N'-t-butyl-N-(1,2,2-trichlorovinyl)carbonyl-N'-benzoylhydrazine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of 1-t-butyl-1-benzoylhydrazine (1.5 g, 0.008 M) in methylene chloride at 5° C. was added, simultaneously and separately, trichloroacryloylchloride (1.7 g, 0.009 M) and triethylamine (0.9 g, 0.009 M). After addition, the reaction was warmed to room temperature and stirred for 3 h. The flask's contents were diluted with 50 ml methylene chloride and washed with water (3×75 ml) and brine solution (1×75 ml). The organic layer was dried over magnesium sulfate and the solvent removed under vacuum to afford N'-t-butyl-N-(1,2,2-trichlorovinyl)carbonyl-N'-benzoylhydrazine as a white solid product.

Workup

  1. additionAfter addition
  2. washwashed with water (3×75 ml) and brine solution (1×75 ml)
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. customthe solvent removed under vacuum

Sources & evidence

ORD record
ord-9eae2fe1d8494c329bf391bb82c7dc5b
Source dataset
uspto-grants-2000_01
Patent number
US06013836

Reaction notes

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