1,1-Dimethylhydrazine → 1,1-Dimethyl-4-(2-methyl-5-phenylbenzyl)semicarbazide

HRID 2296998Notes

Reaction equation

HRID 2296998 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].[CH3:18][N:19]([CH3:21])[NH2:20]>C1(C)C=CC=CC=1>[CH3:18][N:19]([CH3:21])[NH:20][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]

Participants

4

Reactant 2

HCID 59761,1-DimethylhydrazineHCID 120565262-Methyl-5-phenylbenzylisocyanate

Product 1

HCID 183888861,1-Dimethyl-4-(2-methyl-5-phenylbenzyl)semicarbazideYield 49%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a suspension of 7.11 g of crude 2-methyl-5-phenylbenzylisocyanate in 24 ml of toluene was added dropwise 2.10 g (35 mmol) of N,N-dimethylhydrazine with ice-cooling, and the mixture was removed from an ice bath and stirred for 2 hours. The reaction solution was concentrated, and the solid residue was recrystallized from ethanol to obtain 4.41 g (15.6 mmol) of 1,1-dimethyl-4-(2-methyl-5-phenylbenzyl)semicarbazide.

Workup

  1. temperaturecooling
  2. customthe mixture was removed from an ice bath
  3. concentrationThe reaction solution was concentrated
  4. customthe solid residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-d12d5f7406ba49bf9a5ecc6ce89e0d9a
Source dataset
uspto-grants-2002_12
Patent number
US06489487B1

Reaction notes

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