Allylamine → N-[1-(t-Butylazo)cyclohexyl]-N'-allylthiourea

HRID 436736Notes

Reaction equation

HRID 436736 reaction equation
[C:1]([N:5]=[N:6][C:7]1([N:13]=[C:14]=[S:15])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1)([CH3:4])([CH3:3])[CH3:2].[CH2:16]([NH2:19])[CH:17]=[CH2:18]>CCCCC>[C:1]([N:5]=[N:6][C:7]1([NH:13][C:14]([NH:19][CH2:16][CH:17]=[CH2:18])=[S:15])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 7853AllylamineHCID 214311441-t-Butylazo-1-isothiocyanatocyclohexane

Product 1

HCID 21431124N-[1-(t-Butylazo)cyclohexyl]-N'-allylthiourea

Reagents, catalysts & solvents 1

HCID 8003PentaneSolvent2×

Procedure

To 9.6 grams (.0416 moles) of 1-t-butylazo-1-isothiocyanatocyclohexane cooled to 10° C. and stirred with a magnetic stirrer in a 50 ml erlenmeyer flask was added 2.37 grams (.0416 moles) of allylamine. The reaction mixture became viscous, was diluted with pentane and stirred for 24 hours at room temperature. The pentane was stripped from the reaction mixture to leave an orange liquid weighing 11.3 grams (94% crude yield). The infrared spectrum of the product had a strong band at 1525 cm-1 and a sharp NH band at 3300 cm-1 and the isothiocyante band at 2040 cm-1 was very weak indicating a trace of the starting material was still present.

Workup

  1. stirringstirred for 24 hours at room temperature
  2. customto leave an orange liquid

Sources & evidence

ORD record
ord-f2597620455d4496b602af11f74b8b93
Source dataset
uspto-grants-1977_06
Patent number
US04028344

Reaction notes

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