5-(2-Cyclohexylethyl)-1,3,4-thiadiazol-2-amine → 2-(2-cyclohexylethyl)-7-hydroxy-5H-[1,3,4]thiadiazolo[3,2-a]pyrimidin-5-one

HRID 1199101Notes

Reaction equation

HRID 1199101 reaction equation
[NH2:1][C:2]1[S:3][C:4]([CH2:7][CH2:8][CH:9]2[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)=[N:5][N:6]=1.[C:15](OC1C(Cl)=CC(Cl)=CC=1Cl)(=[O:20])[CH2:16][C:17]([O-])=[O:18]>C1(C)C(C)=CC=CC=1>[CH:9]1([CH2:8][CH2:7][C:4]2[S:3][C:2]3=[N:1][C:15]([OH:20])=[CH:16][C:17](=[O:18])[N:6]3[N:5]=2)[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1

Participants

4

Reactant 2

HCID 7506865-(2-Cyclohexylethyl)-1,3,4-thiadiazol-2-amineHCID 198681463-Oxo-3-(2,4,6-trichlorophenoxy)propanoate

Product 1

HCID 1355181302-(2-cyclohexylethyl)-7-hydroxy-5H-[1,3,4]thiadiazolo[3,2-a]pyrimidin-5-oneYield 82%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

2-Amino-5-(2-cyclohexylethyl)-[1,3,4]thiadiazole (9.50 g) and 21.8 g of 2,4,6-trichlorophenyl malonate were stirred in 70 ml of xylene at a bath temperature of from 140° to 150° C. for 2 hours. After cooling, the precipitate formed was collected by filtration and washed successively with ethanol and diethyl ether to obtain 10.3 g of 2-(2-cyclohexylethyl)-7-hydroxy-5H-[1,3,4]thiadiazolo[3,2-a]pyrimidin-5-one as a colorless plate-like crystal.

Workup

  1. temperatureAfter cooling
  2. customthe precipitate formed
  3. filtrationwas collected by filtration
  4. washwashed successively with ethanol and diethyl ether

Sources & evidence

ORD record
ord-0e93562429a64bb8aff098fc59b5d456
Source dataset
uspto-grants-1990_02
Patent number
US04898943

Reaction notes

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