Hydrazinecarboxylic acid, ethyl ester → HCID 54265624, compound

HRID 2255486Notes

Reaction equation

HRID 2255486 reaction equation
[CH:1]1([C:7]2[CH:12]=[CH:11][C:10]([C:13]3[N:14]=[C:15]([N:18]=[CH:19]OCC)[S:16][CH:17]=3)=[CH:9][CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:23]([O:27][CH2:28][CH3:29])(=[O:26])[NH:24][NH2:25]>C(O)C>[CH:1]1([C:7]2[CH:8]=[CH:9][C:10]([C:13]3[N:14]=[C:15]([N:18]=[CH:19][NH:25][NH:24][C:23]([O:27][CH2:28][CH3:29])=[O:26])[S:16][CH:17]=3)=[CH:11][CH:12]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

4

Reactant 2

HCID 20064Hydrazinecarboxylic acid, ethyl esterHCID 54081328HCID 54081328, compound

Product 1

HCID 54265624HCID 54265624, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture consisting of 4-(4-cyclohexylphenyl)-2-ethoxymethyleneaminothiazole (500 mg), ethyl carbazate (170 mg) and ethanol (10 ml) was stirred under ice-cooling for 1 hour and then at room temperature (about 15° C.) for 18 hours. The reaction mixture was concentrated under reduced pressure, and the crystals were collected by filtration with hexane to give ethyl 3-[4-(4-cyclohexylphenyl)-2-thiazolyliminomethyl]carbazate (515 mg, yield of 87 %). Recrystallization from dimethylforamide-water produced colorless prisms, mp of 188 to 189° C.

Workup

  1. temperaturecooling for 1 hour
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. filtrationthe crystals were collected by filtration with hexane

Sources & evidence

ORD record
ord-25e381f5ae9e41d29c8a116086260ba1
Source dataset
uspto-grants-1993_08
Patent number
US05240950

Reaction notes

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