Diethylamine → N-[1-(t-Butylazo)cyclohexyl]-N',N'-diethylurea

HRID 436748Notes

Reaction equation

HRID 436748 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]([NH:18][CH2:19][CH3:20])[CH3:17].[N-]=C=O>CCCCC>[C:1]([N:5]=[N:6][C:7]1([NH:13][C:14]([N:18]([CH2:19][CH3:20])[CH2:16][CH3:17])=[O:15])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 8021DiethylamineHCID 105034IsocyanateHCID 214311721-t-Butylazo-1-isocyanatocyclohexane

Product 1

HCID 21431120N-[1-(t-Butylazo)cyclohexyl]-N',N'-diethylurea

Reagents, catalysts & solvents 1

HCID 8003PentaneSolvent

Procedure

To 7.4 grams (0.0354 moles) of 1-t-butylazo-1-isocyanatocyclohexane stirred with a magnetic stirrer in a 50 ml erlenmeyer flask was added 2.49 grams (0.0354 moles) of diethylamine and the reaction mixture stirred at room temperature. When the reaction mixture became viscous pentane was added. The reaction mixture was stirred for 3 hours and the pentane evaporated under reduced pressure leaving a white wax weighing 10.0 grams (96% crude yield). The infrared spectrum of the product contained a strong carbonyl band at 1640 cm-1 and a sharp NH band at 3380 cm-1. The isocyanate band at 2225 cm-1 was absent.

Workup

  1. additionwas added
  2. stirringThe reaction mixture was stirred for 3 hours
  3. customthe pentane evaporated under reduced pressure
  4. customleaving a white wax

Sources & evidence

ORD record
ord-e9bfb03ab63e474992701d64680504f9
Source dataset
uspto-grants-1977_06
Patent number
US04028344

Reaction notes

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