Hydrochloric Acid → HCID 21501700, compound

HRID 1288396Notes

Reaction equation

HRID 1288396 reaction equation
[Cl:1][CH2:2][N:3]([CH2:15][CH2:16][CH:17]=[O:18])[C:4]([NH:6][C:7]1[S:8][C:9]([CH2:12][CH:13]=[CH2:14])=[N:10][N:11]=1)=[O:5].Cl>O>[CH2:12]([C:9]1[S:8][C:7]([N:6]2[CH:17]([OH:18])[CH2:16][CH2:15][N:3]([CH2:2][Cl:1])[C:4]2=[O:5])=[N:11][N:10]=1)[CH:13]=[CH2:14]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 21501685HCID 21501685, compound

Product 1

HCID 21501700HCID 21501700, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The dimethyl acetal of 3-[1-chloromethyl-3-(5-allyl-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-allyl-1,3,4-thiadiazol-2-yl)-3-chloromethyl-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-9b0df758e7434e208c896e5c85532e73
Source dataset
uspto-grants-1976_10
Patent number
US03988143

Reaction notes

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