Hydrochloric Acid → HCID 21481882, compound

HRID 1415359Notes

Reaction equation

HRID 1415359 reaction equation
[CH2:1]([N:4]([CH2:18][CH2:19][CH:20]=[O:21])[C:5]([NH:7][C:8]1[S:9][C:10]([CH:13]2[CH2:17][CH2:16][CH2:15][CH2:14]2)=[N:11][N:12]=1)=[O:6])[CH2:2][CH3:3].Cl>O>[CH:13]1([C:10]2[S:9][C:8]([N:7]3[CH:20]([OH:21])[CH2:19][CH2:18][N:4]([CH2:1][CH2:2][CH3:3])[C:5]3=[O:6])=[N:12][N:11]=2)[CH2:14][CH2:15][CH2:16][CH2:17]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 21481899HCID 21481899, compound

Product 1

HCID 21481882HCID 21481882, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The dimethyl acetal of 3-[1-propyl-3-(5-cyclopentyl-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-cyclopentyl-1,3,4-thiadiazol-2-yl)-3-propyl-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-581ee112c4d24e859ca81d6e8dd22747
Source dataset
uspto-grants-1977_01
Patent number
US04004912

Reaction notes

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