Cyclohexylamine → N-[1-(t-Butylazo)cyclohexyl]-N'-cyclohexylthiourea

HRID 436730Notes

Reaction equation

HRID 436730 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].[CH:16]1([NH2:22])[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1.[N-]=C=S>CCCCC>[C:1]([N:5]=[N:6][C:7]1([NH:13][C:14]([NH:22][CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)=[S:15])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 7965CyclohexylamineHCID 214311441-t-Butylazo-1-isothiocyanatocyclohexaneHCID 178418790HCID 178418790, compound

Product 1

HCID 21431194N-[1-(t-Butylazo)cyclohexyl]-N'-cyclohexylthiourea

Reagents, catalysts & solvents 1

HCID 8003PentaneSolvent2×

Procedure

To 8.4 grams (0.0363 moles) of 1-t-butylazo-1-isothiocyanatocyclohexane stirred with a magnetic stirrer in a 50 ml erlenmeyer flask was added 3.6 grams (0.0363 moles) of cyclohexylamine 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 11.4 grams (95% crude yield). The product melted at 100°-102° C. and the infrared spectrum of the product had a strong broad band at 1520-1540 cm-1 and a NH band at 3220 cm-1. The isothiocyanate band at 2040 cm-1 was absent.

Workup

  1. customto form
  2. customto leave a yellow solid

Sources & evidence

ORD record
ord-9e570efb17444ed2803d0a03b370db7a
Source dataset
uspto-grants-1977_06
Patent number
US04028344

Reaction notes

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