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

HRID 1906526Notes

Reaction equation

HRID 1906526 reaction equation
[NH2:1][C:2]1[S:3][C:4]([C:7]2[CH:12]=[CH:11][C:10]([C:13]([CH3:16])([CH3:15])[CH3:14])=[CH:9][CH:8]=2)=[N:5][N:6]=1.[C:17](OC1C(Cl)=CC(Cl)=CC=1Cl)(=[O:22])[CH2:18][C:19]([O-])=[O:20]>C1C=CC(C2C=CC=CC=2)=CC=1.C1C=CC(OC2C=CC=CC=2)=CC=1>[C:13]([C:10]1[CH:11]=[CH:12][C:7]([C:4]2[S:3][C:2]3=[N:1][C:17]([OH:22])=[CH:18][C:19](=[O:20])[N:6]3[N:5]=2)=[CH:8][CH:9]=1)([CH3:16])([CH3:15])[CH3:14]

Participants

4

Reactant 2

HCID 8111605-(4-tert-Butylphenyl)-1,3,4-thiadiazol-2-amineHCID 198681463-Oxo-3-(2,4,6-trichlorophenoxy)propanoate

Product 1

HCID 1358024502-(4-tert-butylphenyl)-7-hydroxy-5H-[1,3,4]thiadiazolo[3,2-a]pyrimidin-5-oneYield 96.6%

Reagents, catalysts & solvents 1

HCID 246701,1'-Biphenyl, mixt. with 1,1'-oxybis(benzene)Solvent

Procedure

A mixture of 9.3 g of 2-amino-5-(4-tert-butylphenyl)-1,3,4-thiadiazole, 20 g of 2,4,6-trichlorophenyl malonate and 50 ml of Dowtherm A was heated at a temperature of 120° to 130° C. for 2 hours. After allowing the mixture to cool, the precipitate was separated by filtration, washed successively with isopropanol and diethyl ether to obtain 11.6 g of 2-(4-tert-butylphenyl)-7-hydroxy-5H-[1,3,4]thiadiazolo[3,2-a]pyrimidin-5-one as a colorless, crystalline powder having a melting point of 265° to 268° C. (decomposition).

Workup

  1. temperaturewas heated at a temperature of 120° to 130° C. for 2 hours
  2. temperatureto cool
  3. customthe precipitate was separated by filtration
  4. washwashed successively with isopropanol and diethyl ether

Sources & evidence

ORD record
ord-eff97c3f4dcd41f99dd3a61bda38d05a
Source dataset
uspto-grants-1987_03
Patent number
US04652646

Reaction notes

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