Urea → N-[1-(t-Butylazo)cyclohexyl]-N'-isobutylurea

HRID 436745Notes

Reaction equation

HRID 436745 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].[CH2:16]([NH2:20])[CH:17]([CH3:19])[CH3:18].NC(N)=O.[N-]=C=O>CCCCC>[C:1]([N:5]=[N:6][C:7]1([NH:13][C:14]([NH:20][CH2:16][CH:17]([CH3:19])[CH3:18])=[O:15])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 1176UreaHCID 6558IsobutylamineHCID 105034IsocyanateHCID 214311721-t-Butylazo-1-isocyanatocyclohexane

Product 1

HCID 21431209N-[1-(t-Butylazo)cyclohexyl]-N'-isobutylurea

Reagents, catalysts & solvents 1

HCID 8003PentaneSolvent2×

Procedure

To 7.4 grams (0.0353 moles) of 1-t-butylazo-1-isocyanatocyclohexane stirred with a magnetic stirrer in a 50 ml erlenmeyer flask was added 2.59 grams (0.0353 moles) of isobutylamine. The reaction mixture became viscous, was diluted with pentane and stirred for 3 hours at room temperature. The pentane was stripped from the reaction mixture leaving a yellow solid weighing 9.7 grams (97% crude yield). The product melted at 90°-92° C. The infrared spectrum of the product contained a very strong urea type carbonyl around 1625 cm-1 and a broad NH band at 3330 cm-1. The isocyanate band at 2225 cm-1 was absent.

Workup

  1. customleaving a yellow solid

Sources & evidence

ORD record
ord-061d49c574c44f6fb443f90c08d772dd
Source dataset
uspto-grants-1977_06
Patent number
US04028344

Reaction notes

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