Acetohydrazide → 1-Acetyl-4-(2-methyl-5-phenylbenzyl)semicarbazide

HRID 2296999Notes

Reaction equation

HRID 2296999 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:8][C:3]=1[CH2:4][N:5]=[C:6]=[O:7].[C:18]([NH:21][NH2:22])(=[O:20])[CH3:19]>O1CCCC1>[C:18]([NH:21][NH:22][C:6]([NH:5][CH2:4][C:3]1[CH:8]=[C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:10]=[CH:11][C:2]=1[CH3:1])=[O:7])(=[O:20])[CH3:19]

Participants

4

Reactant 2

HCID 14039AcetohydrazideHCID 120565262-Methyl-5-phenylbenzylisocyanate

Product 1

HCID 183888341-Acetyl-4-(2-methyl-5-phenylbenzyl)semicarbazideYield 28.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2.47 g (11.1 mmol) of crude 2-methyl-5-phenylbenzylisocyanate in 50 ml of tetrahydrofuran was added 0.82 g of acetohydrazide and the mixture was heated under reflux for 1 hour. After allowing to cool to room temperature, the reaction mixture was concentrated, and the residue was recrystallized from ethanol to obtain 0.93 g (3.13 mmol) of 1-acetyl-4-(2-methyl-5-phenylbenzyl)semicarbazide.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 1 hour
  3. concentrationthe reaction mixture was concentrated
  4. customthe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-6c155dd91e814c37a8bb3246f34268f6
Source dataset
uspto-grants-2002_12
Patent number
US06489487B1

Reaction notes

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