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

HRID 972416Notes

Reaction equation

HRID 972416 reaction equation
[CH3:1][C:2]([N:6]([CH2:19][CH2:20][CH:21]=[O:22])[C:7]([NH:9][C:10]1[S:11][C:12]([C:15]([F:18])([F:17])[F:16])=[N:13][N:14]=1)=[O:8])([CH3:5])[C:3]#[CH:4].Cl>O>[F:16][C:15]([F:18])([F:17])[C:12]1[S:11][C:10]([N:9]2[CH:21]([OH:22])[CH2:20][CH2:19][N:6]([C:2]([CH3:1])([CH3:5])[C:3]#[CH:4])[C:7]2=[O:8])=[N:14][N:13]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 214000743-[1-(1,1-Dimethylprop-2-ynyl)-3-(5-trifluoromethyl-1,3,4-thiadiazol-2-yl)ureido]propionaldehyde

Product 1

HCID 21400099tetrahydro-1-(5-trifluoromethyl-1,3,4-thiadiazol-2-yl)-3-(1,1-dimethylprop-2-ynyl)-6-hydroxy-2(1H)-pyrimidinone

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The diethyl acetal of 3-[1-(1,1-dimethylprop-2-ynyl)-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 to form 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-(1,1-dimethylprop-2-ynyl)-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. customto form a precipitate
  8. filtrationThe precipitate is recovered by filtration
  9. customis dried
  10. customis recrystallized

Sources & evidence

ORD record
ord-416563ddefd84ceaad6026659fd053a2
Source dataset
uspto-grants-1977_10
Patent number
US04053298

Reaction notes

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