Tert-Butylamine → N-[1-(t-Butylazo)cyclohexyl]-N'-t-butylthiourea

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

Participants

Procedure

To 9.1 grams (0.0394 moles) of 1-t-butylazo-1isothiocyanatocyclohexane stirred with a magnetic stirrer in a 50 ml erlenmeyer flask was added 2.88 grams (0.0394 moles) of t-butylamine at room temperature. A solid slowly started to form and pentane was added to keep the reaction mixture from solidifying and the reaction mixture was stirred for 3 hours and the pentane stripped off to leave a yellow solid weighing 10.9 grams (91% crude yield). The product melted at 95°-98° C. and the infrared spectrum of the product had strong bands at 1520 and 1550 cm-1 and a sharp NH band at 3300 cm-1. There was a small amount of unreacted starting material presence, indicated by the presence of a weak isothiocyanate band at 2040 cm-1.