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

HRID 1883634Notes

Reaction equation

[CH3:1][NH:2][NH2:3].[CH3:4][C:5]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:11][C:6]=1[CH2:7][N:8]=[C:9]=[O:10].CCCCCC.C(OCC)(=O)C.C(OCC)(=O)C>C1(C)C=CC=CC=1>[CH3:1][N:2]([C:9]([NH:8][CH2:7][C:6]1[CH:11]=[C:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:13]=[CH:14][C:5]=1[CH3:4])=[O:10])[NH2:3]

Participants

Conditions

Temperature: 0 °C

Procedure

254 mg (5.52 mmol) of methylhydrazine was dissolved in 10 ml of anhydrous toluene, and the mixture was cooled to 0° C. Tot this solution was slowly dropped while stirring a solution prepared by dissolving 1.12 g (5.02 mmol) of 2-methyl-5-phenylbenzyl isocyanate in 20 ml of anhydrous toluene. In this operation, the temperature of the reaction solution was controlled in the range from 0 to 5° C. After completion of dropping, the solution was stirred at 0° C. for 1 hour, further, stirring was continued for 2 hours at room temperature. The reaction solution was concentrated, and the residue was subjected to silica gel column chromatography (eluant: hexane/ethyl acetate=1/1, then, 1/2 (v/v), then only ethyl acetate), to obtain 1.28 g (4.75 mmol) of 2-methyl-4-(2-methyl-5-phenylbenzyl) semicarbazide having a melting point of 91.6° C.

Workup

additionTot this solution was slowly dropped
customprepared
customwas controlled in the range from 0 to 5° C
stirringthe solution was stirred at 0° C. for 1 hour
stirringfurther, stirring
concentrationThe reaction solution was concentrated

Sources & evidence

ORD record: ord-8a5ea735e584422db0e781d958214cef
Source dataset: uspto-grants-2004_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06762197B2

Reaction notes

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