Water → 2-(1-(3-(Trifluoromethyl)phenyl)ethylidene)hydrazinecarboxylic acid ethyl ester

HRID 52768

Reaction equation

HRID 52768 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:4]=[C:5]([C:9](=O)[CH3:10])[CH:6]=[CH:7][CH:8]=1.[C:14]([O:18][CH2:19][CH3:20])(=[O:17])[NH:15][NH2:16].O>C1(C)C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH2:19]([O:18][C:14]([NH:15][N:16]=[C:9]([C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:13])([F:12])[F:1])[CH:4]=1)[CH3:10])=[O:17])[CH3:20]

Participants

6

Reactant 3

HCID 962WaterHCID 20064Hydrazinecarboxylic acid, ethyl esterHCID 676823'-(Trifluoromethyl)acetophenone

Product 1

HCID 544126252-(1-(3-(Trifluoromethyl)phenyl)ethylidene)hydrazinecarboxylic acid ethyl esterYield 100%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 1140TolueneSolvent

Procedure

m-Trifluoromethylacetophenone (74 g, 0.394 mole), ethyl carbazate (43 g, 0.413 mole), and catalytic p-toluenesulfonic acid (20 mg) were refluxed under N2 over a Dean-Stark trap in toluene (1.2 L) until the theoretical amount of water of reaction was removed (7.1 mL, 6 h). The solvent was then removed in vacuo and 2-(1-(3-(trifluoromethyl)phenyl)ethylidene)hydrazinecarboxylic acid ethyl ester (107 g, 100% yield) was obtained as a white solid which was recrystallized from cyclohexane, mp=94°-96° C.

Workup

  1. customwas removed (7.1 mL, 6 h)
  2. customThe solvent was then removed in vacuo

Sources & evidence

ORD record
ord-640195158d9c4938b040650e31783986
Source dataset
uspto-grants-1997_04
Patent number
US05616789

Linked notes

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