Oxalyl chloride → N'-t-butyl-N-benzoyl-N'-(beta-trifluoromethylcrotonyl)hydrazine

HRID 849770

Reaction equation

HRID 849770 reaction equation
[C:1]([NH:5][NH:6][C:7](=[O:14])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([CH3:4])([CH3:3])[CH3:2].[F:15][C:16]([F:24])([F:23])/[C:17](/[CH3:22])=[CH:18]\[C:19](Cl)=[O:20].C(Cl)(=O)C(Cl)=O.FC(F)(F)/C(/C)=C\C(O)=O>C1(C)C=CC=CC=1>[C:1]([N:5]([C:19](=[O:20])/[CH:18]=[C:17](\[C:16]([F:24])([F:23])[F:15])/[CH3:22])[NH:6][C:7](=[O:14])[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 65578Oxalyl chlorideHCID 299436N'-tert-butylbenzohydrazideHCID 57088354,4,4-Trifluoro-3-methyl-2-butenoic acidHCID 86745869beta-Trifluoromethylcrotonyl chloride

Product 1

HCID 70294050N'-t-butyl-N-benzoyl-N'-(beta-trifluoromethylcrotonyl)hydrazine

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

N'-t-butyl-N-benzoylhydrazine (1.0 g,) in 2 ml toluene was added dropwise to a solution of beta-trifluoromethylcrotonyl chloride (prepared by addition of oxalyl chloride (1.3 g) to a solution of 1.5 g beta-trifluoromethylcrotonic acid in 5 ml toluene at 23° C.). After 30 min. at 23° C., the reaction mixture was partitioned between saturated aqueous sodium bicarbonate (20 ml) and ether (20 ml). The ether layer was evaporated under reduced pressure to about 10 ml and the excess hydrazine was removed by filtration. The filtrate was evaporated to give N'-t-butyl-N-benzoyl-N'-(beta-trifluoromethylcrotonyl)hydrazine as a colorless oil.

Workup

  1. customthe reaction mixture was partitioned between saturated aqueous sodium bicarbonate (20 ml) and ether (20 ml)
  2. customThe ether layer was evaporated under reduced pressure to about 10 ml
  3. customthe excess hydrazine was removed by filtration
  4. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-a0ec4bd5c3bd41b99ae4fbc230312fe8
Source dataset
uspto-grants-2000_01
Patent number
US06013836

Linked notes

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