Ethylenediamine → 1,1'-Ethylenebis[3-(1-t-butylazocyclohexyl)urea]

HRID 436747Notes

Reaction equation

HRID 436747 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]([NH2:19])[CH2:17][NH2:18]>CCCCC>[CH2:16]([NH:19][C:14]([NH:13][C:7]1([N:6]=[N:5][C:1]([CH3:4])([CH3:3])[CH3:2])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1)=[O:15])[CH2:17][NH:18][C:14]([NH:13][C:7]1([N:6]=[N:5][C:1]([CH3:4])([CH3:2])[CH3:3])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1)=[O:15]

Participants

4

Reactant 2

HCID 3301EthylenediamineHCID 214311721-t-Butylazo-1-isocyanatocyclohexane

Product 1

HCID 214313231,1'-Ethylenebis[3-(1-t-butylazocyclohexyl)urea]

Reagents, catalysts & solvents 1

HCID 8003PentaneSolvent3×

Procedure

To 8.4 grams (0.0402 moles) of 1-t-butylazo-1-isocyanatocyclohexane stirred with a magnetic stirrer in a 50 ml erlenmeyer flask was added 1.57 grams (0.0201 moles) of ethylenediamine. Solids formed and the reaction mixture was diluted with pentane and stirred for 3 hours at room temperature. The pentane was stripped from the reaction mixture leaving a semi-solid. The semi-solid was slurried in cold pentane and filtered. The white solid filter cake was air dried and weighed 10.0 grams (75% crude yield). The product melted at 165°-167° C. with decomposition. The infrared spectrum of the product contained a strong carbonyl band at 1670 cm-1 and NH bands at 3300 and 3340 cm-1. The isocyanate band at 2225 cm-1 was absent.

Workup

  1. customSolids formed
  2. customleaving a semi-solid
  3. filtrationfiltered
  4. filtrationThe white solid filter cake
  5. customdried

Sources & evidence

ORD record
ord-642999f0bbe4446c9aad758042e566bb
Source dataset
uspto-grants-1977_06
Patent number
US04028344

Reaction notes

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