Hydrochloric Acid → tetrahydro-1-(5-trifluoromethyl-1,3,4-thiadiazol-2-yl)-3-methyl-6-hydroxy-2(1H)-pyrimidinone

HRID 435534Notes

Reaction equation

HRID 435534 reaction equation
[CH3:1][N:2]([CH2:15][CH2:16][CH:17]=[O:18])[C:3]([NH:5][C:6]1[S:7][C:8]([C:11]([F:14])([F:13])[F:12])=[N:9][N:10]=1)=[O:4].Cl>O>[F:14][C:11]([F:12])([F:13])[C:8]1[S:7][C:6]([N:5]2[CH:17]([OH:18])[CH2:16][CH2:15][N:2]([CH3:1])[C:3]2=[O:4])=[N:10][N:9]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 214000943-[1-Methyl-3-(5-trifluoromethyl-1,3,4-thiadiazol-2-yl)ureido]propionaldehyde

Product 1

HCID 21400101tetrahydro-1-(5-trifluoromethyl-1,3,4-thiadiazol-2-yl)-3-methyl-6-hydroxy-2(1H)-pyrimidinone

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The dimethyl acetal of 3-[1-methyl-3-(5-trifluoromethyl-1,3,4-thiadiazol-2-yl)ureido]propionaldehyde (15 grams), water (400 ml) and hydrochloric acid (4 ml) are charged into a glass reaction vessel equipped with a mechanical stirrer, thermometer and reflux condenser. The reaction mixture is heated at reflux for a period of about 15 minutes. The reaction mixture is then filtered while hot and the filtrate is cooled resulting in the formation of a precipitate. The precipitate is recovered by filtration, is dried and is recrystallized to yield the desired product tetrahydro-1-(5-trifluoromethyl-1,3,4-thiadiazol-2-yl)-3-methyl-6-hydroxy-2(1H)-pyrimidinone.

Workup

  1. customequipped with a mechanical stirrer
  2. temperaturethermometer and reflux condenser
  3. temperatureThe reaction mixture is heated
  4. temperatureat reflux for a period of about 15 minutes
  5. filtrationThe reaction mixture is then filtered while hot and the filtrate
  6. temperatureis cooled
  7. customresulting in the formation of a precipitate
  8. filtrationThe precipitate is recovered by filtration
  9. customis dried
  10. customis recrystallized

Sources & evidence

ORD record
ord-9f3bbcc8a19c4315a313ddbfe2557f6a
Source dataset
uspto-grants-1977_02
Patent number
US04006009

Reaction notes

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