Isobutylamine → N-[1-(t-Butylazo)cyclohexyl]-N'-isobutylthiourea

HRID 436732Notes

Reaction equation

HRID 436732 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]([NH2:20])[CH:17]([CH3:19])[CH3:18].[N-]=C=S>CCCCC>[C:1]([N:5]=[N:6][C:7]1([NH:13][C:14]([NH:20][CH2:16][CH:17]([CH3:19])[CH3:18])=[S:15])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 6558IsobutylamineHCID 214311441-t-Butylazo-1-isothiocyanatocyclohexaneHCID 178418790HCID 178418790, compound

Product 1

HCID 21431317N-[1-(t-Butylazo)cyclohexyl]-N'-isobutylthiourea

Reagents, catalysts & solvents 1

HCID 8003PentaneSolvent2×

Procedure

To 9.1 grams (.0394 moles) of 1-t-butylazo-1-isothiocyanatocyclohexane stirred with a magnetic stirrer in a 50 ml erlenmeyer flask was added 2.88 grams (.0394 moles) of isobutylamine at room temperature. The reaction mixture became viscous so pentane was added and the reaction was stirred an additional 4 hours and the pentane stripped off to leave a yellow solid weighing 11.6 grams (97% crude yield). The product melted at 90°-93° C. and the infrared spectrum of the product had a strong broad band at 1520-1550 cm-1 and a NH band at 3270 cm-1. There was only a trace of the isothiocyanate band at 2040 cm-1 which was present in the starting material.

Workup

  1. additionwas added
  2. customto leave a yellow solid

Sources & evidence

ORD record
ord-6429e22d6f8244588a68f7871cf69c01
Source dataset
uspto-grants-1977_06
Patent number
US04028344

Reaction notes

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