Methylhydrazine → 4-[1-(t-Butylazo)cyclohexyl]-2-methylsemicarbazide

HRID 436749Notes

Reaction equation

[C:1]([N:5]=[N:6][C:7]1([N:13]=[C:14]=[O:15])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1)([CH3:4])([CH3:3])[CH3:2].[CH3:16][NH:17][NH2:18].[N-]=C=O>CCCCC>[C:1]([N:5]=[N:6][C:7]1([NH:13][C:14](=[O:15])[N:17]([CH3:16])[NH2:18])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1)([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 5 °C

Procedure

To 8.2 grams (0.0392 moles) of 1-t-butylazo-1-isocyanatocyclohexane stirred with a magnetic stirrer in a 50 ml erlenmeyer flask and cooled to 5° C. was added 1.82 grams (0.0392 moles) of methylhydrazine. The reaction was very rapid and exothermic and became quite viscous. The reaction mixture was diluted with pentane and stirred for an additional 60 minutes at room temperature. The pentane was evaporated under reduced pressure leaving 9.0 grams (90% crude yield) of a yellow solid. The product melted at 169°-171° C. with decomposition. The infrared spectrum of the product contained a strong carbonyl band at 1660 cm-1 and a moderate NH band at 3320 cm-1. The isocyanate band at 2225 cm-1 was absent.

Workup

customThe pentane was evaporated under reduced pressure
customleaving 9.0 grams (90% crude yield) of a yellow solid

Sources & evidence

ORD record: ord-8d416c253721430bb3e24f8c083b70fb
Source dataset: uspto-grants-1977_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04028344

Reaction notes

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