Diethylamine → N-[1-(t-Butylazo)cyclohexyl]-N',N'-diethylthiourea

HRID 436734Notes

Reaction equation

HRID 436734 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]([NH:18][CH2:19][CH3:20])[CH3:17].[N-]=C=S>CCCCC>[C:1]([N:5]=[N:6][C:7]1([NH:13][C:14]([N:18]([CH2:19][CH3:20])[CH2:16][CH3:17])=[S:15])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 8021DiethylamineHCID 214311441-t-Butylazo-1-isothiocyanatocyclohexaneHCID 178418790HCID 178418790, compound

Product 1

HCID 21431311N-[1-(t-Butylazo)cyclohexyl]-N',N'-diethylthiourea

Reagents, catalysts & solvents 1

HCID 8003PentaneSolvent2×

Procedure

To 9.12 grams (.0395 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 2.89 grams (.0395 moles) of diethylamine. The reaction mixture was stirred for 3 hours at room temperature, adding pentane periodically to keep the viscosity low. The pentane was stripped from the reaction mixture to leave a yellow viscous oil weighing 11.4 grams (95% crude yield). The infrared spectrum of the product had a strong broad band at 1520 cm-1 and a sharp NH band at 3300 cm-1 and the isothiocyanate band at 2040 cm-1 was very weak indicating there was a trace of the starting material still present.

Workup

  1. stirringThe reaction mixture was stirred for 3 hours at room temperature
  2. customto leave a yellow viscous oil

Sources & evidence

ORD record
ord-fdfba77b7e3049248d010ffd081696c7
Source dataset
uspto-grants-1977_06
Patent number
US04028344

Reaction notes

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