Water → 2-Methyl-4-(2-methyl-5-phenylbenzyl)semicarbazide

HRID 1883636Notes

Reaction equation

HRID 1883636 reaction equation
[C-]#N.[Na+].[C:4]1([CH3:10])[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH3:11][NH:12][NH2:13].O.[CH3:15][N:16](C)[CH:17]=[O:18]>>[CH3:11][N:12]([C:17]([NH:16][CH2:15][C:5]1[CH:6]=[C:7]([C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH:8]=[CH:9][C:4]=1[CH3:10])=[O:18])[NH2:13]

Participants

6

Reactant 5

HCID 962WaterHCID 1140TolueneHCID 6061MethylhydrazineHCID 6228DimethylformamideHCID 8929Sodium Cyanide

Product 1

HCID 178349412-Methyl-4-(2-methyl-5-phenylbenzyl)semicarbazide

Conditions

Temperature
100 °C

Procedure

1.0 g (4.61 mmol) of 2-methyl-5-phenylbenzyl chloride (produced in the same manner as in Intermediate Production Example 10) is dissolved in 2 ml of anhydrous N,N-dimethylformamide, and to this solution is added 450 mg (6.92 mmol) of sodium cyanide, and the mixture is stirred at 100° C. Subsequently, 2 ml of toluene is added to the reaction solution and the mixture is cooled to 0° C., to this is added 213 mg (4.61 mmol) of methylhydrazine, the mixture is stirred at room temperature, then, to this is added water, and the mixture is extracted with chloroform. The organic layer is washed with saturated saline, end-dried over anhydrous magnesium sulfate, and concentrated to obtain 2-methyl-4-(2-methyl-5-phenylbenzyl) semicarbazide.

Workup

  1. temperaturethe mixture is cooled to 0° C.
  2. stirringthe mixture is stirred at room temperature
  3. extractionthe mixture is extracted with chloroform
  4. washThe organic layer is washed with saturated saline
  5. dry with materialend-dried over anhydrous magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-891aca8b8f024b228b0c61f0fb8ada3f
Source dataset
uspto-grants-2004_07
Patent number
US06762197B2

Reaction notes

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