Hydrochloric Acid → tetrahydro-1-(5-methoxy-1,3,4-thiadiazol-2-yl)-3-but-3-enyl-6-hydroxy-2(1H)-pyrimidinone

HRID 972413Notes

Reaction equation

HRID 972413 reaction equation
[CH2:1]([N:5]([CH2:16][CH2:17][CH:18]=[O:19])[C:6]([NH:8][C:9]1[S:10][C:11]([O:14][CH3:15])=[N:12][N:13]=1)=[O:7])[CH2:2][CH:3]=[CH2:4].Cl>O>[CH3:15][O:14][C:11]1[S:10][C:9]([N:8]2[CH:18]([OH:19])[CH2:17][CH2:16][N:5]([CH2:1][CH2:2][CH:3]=[CH2:4])[C:6]2=[O:7])=[N:13][N:12]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 214001093-[1-But-3-enyl-3-(5-methoxy-1,3,4-thiadiazol-2-yl)ureido]propionaldehyde

Product 1

HCID 21400096tetrahydro-1-(5-methoxy-1,3,4-thiadiazol-2-yl)-3-but-3-enyl-6-hydroxy-2(1H)-pyrimidinone

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The diethyl acetal of 3-[1-but-3-enyl-3-(5-methoxy-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-methoxy-1,3,4-thiadiazol-2-yl)-3-but-3-enyl-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-ad0b3f3ec258411a867fadfa940ec946
Source dataset
uspto-grants-1977_10
Patent number
US04053298

Reaction notes

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