Aniline → N-[1-(t-Butylazo)cyclohexyl]-N'-phenylurea

HRID 436750Notes

Reaction equation

HRID 436750 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].[NH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CCCCC>[C:1]([N:5]=[N:6][C:7]1([NH:13][C:14]([NH:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:15])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 6115AnilineHCID 214311721-t-Butylazo-1-isocyanatocyclohexane

Product 1

HCID 21431183N-[1-(t-Butylazo)cyclohexyl]-N'-phenylurea

Reagents, catalysts & solvents 1

HCID 8003PentaneSolvent

Procedure

To 6.9 grams (0.033 moles) of 1-t-butylazo-1-isocyanatocyclohexane stirred with a magnetic stirrer in a 50 ml erlenmeyer flask was added 3.08 grams (0.033 moles) aniline. The reaction mixture was stirred for three days at room temperature. The solid mass that formed was slurried in pentane and filtered. The filter cake was air dried and weighed 9.2 grams (92% crude yield). The product melted at 169°-171° C. with decomposition and the infrared spectrum of the product contained a strong carbonyl band at 1650 cm-1 and a sharp NH band at 3320 cm-1 and the isocyanate band at 2225 cm-1 of the starting material was absent.

Workup

  1. customThe solid mass that formed
  2. filtrationfiltered
  3. customdried

Sources & evidence

ORD record
ord-6ccc8718bb814d669f474d7cd3b3a771
Source dataset
uspto-grants-1977_06
Patent number
US04028344

Reaction notes

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