Ammonia → 5-(2-Cyclohexylethyl)-1,3,4-thiadiazol-2-amine

HRID 1199105Notes

Reaction equation

HRID 1199105 reaction equation
[CH:1]1([CH2:7][CH2:8][C:9]#[N:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.N[NH:12][C:13]([NH2:15])=[S:14].N>FC(F)(F)C(O)=O>[CH:1]1([CH2:7][CH2:8][C:9]2[S:14][C:13]([NH2:15])=[N:12][N:10]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 2723789ThiosemicarbazideHCID 107492423-Cyclohexylpropanenitrile

Product 1

HCID 7506865-(2-Cyclohexylethyl)-1,3,4-thiadiazol-2-amineYield 70.8%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

3-Cyclohexylpropionitrile (181 g) and 120 g of thiosemicarbazide were dissolved in 40 ml of trifluoroacetic acid, followed by stirring at a bath temperature of 70° to 80° C. for 4 hours. The reaction mixture was poured into ice-water, and 500 ml of concentrated aqueous ammonia was added thereto, followed by stirring at room temperature for 1.5 hours. The resulting precipitate was collected by filtration and washed with successive, small amounts of ethanol and diethyl ether to obtain 197 g of the titled compound.

Workup

  1. additionwas added
  2. stirringby stirring at room temperature for 1.5 hours
  3. filtrationThe resulting precipitate was collected by filtration
  4. washwashed with successive, small amounts of ethanol and diethyl ether

Sources & evidence

ORD record
ord-bc96256b63824bf0bf4273e33ae334a8
Source dataset
uspto-grants-1990_02
Patent number
US04898943

Reaction notes

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