Phenylhydrazine → 4-[1-(t-Butylazo)cyclohexyl]-1-phenylsemicarbazide

HRID 436746Notes

Reaction equation

HRID 436746 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].[C:16]1([NH:22][NH2:23])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>CCCCC>[C:1]([N:5]=[N:6][C:7]1([NH:13][C:14](=[O:15])[NH:23][NH:22][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 7516PhenylhydrazineHCID 214311721-t-Butylazo-1-isocyanatocyclohexane

Product 1

HCID 214311824-[1-(t-Butylazo)cyclohexyl]-1-phenylsemicarbazide

Reagents, catalysts & solvents 1

HCID 8003PentaneSolvent

Procedure

To 6.6 grams (0.0315 moles) of 1-t-butylazo-1-isocyanatocyclohexane cooled to 5° C. and stirred with a magnetic stirrer in a 50 ml erlenmeyer flask was added dropwise 3.42 grams (0.0315 moles) of phenylhydrazine. The reaction was very exothermic and rapid. Pentane was added to slurry the solid product and the slurry was filtered. The white solid filter cake was air dried and weighed 10.0 grams (100% crude yield). The product melted at 140°-142° C. with decomposition. The infrared spectrum of the product contained a strong carbonyl band at 1670 cm-1 and NH bands at 3100, 3230 and 3320 cm-1. The isocyanate band at 2225 cm-1 was absent.

Workup

  1. filtrationthe slurry was filtered
  2. filtrationThe white solid filter cake
  3. customdried

Sources & evidence

ORD record
ord-20e49b29087a41aa99a4bb869c9ff367
Source dataset
uspto-grants-1977_06
Patent number
US04028344

Reaction notes

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