Ethylenediamine → 1,1'-Ethylenebis-[3-(1-t-butylazocyclohexyl)thiourea]

HRID 436735Notes

Reaction equation

HRID 436735 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])[CH2:17][NH2:18].[N-:20]=[C:21]=[S:22]>CCCCC>[CH2:16]([NH:19][C:21]([NH:20][C:7]1([N:6]=[N:5][C:1]([CH3:4])([CH3:3])[CH3:2])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1)=[S:22])[CH2:17][NH:18][C:14]([NH:13][C:7]1([N:6]=[N:5][C:1]([CH3:4])([CH3:2])[CH3:3])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]1)=[S:15]

Participants

5

Reactant 3

HCID 3301EthylenediamineHCID 214311441-t-Butylazo-1-isothiocyanatocyclohexaneHCID 178418790HCID 178418790, compound

Product 1

HCID 214311341,1'-Ethylenebis-[3-(1-t-butylazocyclohexyl)thiourea]

Reagents, catalysts & solvents 1

HCID 8003PentaneSolvent2×

Procedure

To 10.25 grams (.044 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 1.73 grams (.0222 moles) of ethylenediamine. The reaction mixture became viscous, pentane was added and the reaction mixture stirred for 6 hours at room temperature. The pentane was stripped from the reaction mixture to leave a yellow solid weighing 10.7 grams (90% crude yield). The product melted at 149°-152° C. with decomposition and its infrared spectrum had a strong band at 1530 cm-1 and moderate NH bands at 3350 cm-1 and the isothiocyanate band at 2040 cm-1 was absent.

Workup

  1. stirringthe reaction mixture stirred for 6 hours at room temperature
  2. customto leave a yellow solid

Sources & evidence

ORD record
ord-11ee21f8334d444e811c79221d23edbf
Source dataset
uspto-grants-1977_06
Patent number
US04028344

Reaction notes

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