Hydrochloric Acid → HCID 21453433, compound

HRID 436230Notes

Reaction equation

HRID 436230 reaction equation
[CH3:1][N:2]([CH2:13][CH:14]=[O:15])[C:3]([NH:5][C:6]1[S:7][C:8]([CH2:11][Cl:12])=[N:9][N:10]=1)=[O:4].Cl>O>[Cl:12][CH2:11][C:8]1[S:7][C:6]([N:5]2[CH:14]([OH:15])[CH2:13][N:2]([CH3:1])[C:3]2=[O:4])=[N:10][N:9]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 20392685HCID 20392685, compound

Product 1

HCID 21453433HCID 21453433, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The dimethyl acetal of 2-[1-methyl-3-(5-chloromethyl-1,3,4-thiadiazol-2-yl)ureido]acetaldehyde (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 from an ethyl acetate-hexane mixture to yield the desired product 1-(5-chloromethyl-1,3,4-thiadiazol-2-yl)-3-methyl-5-hydroxy-1,3-imidazolidin-2-one.

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 from an ethyl acetate-hexane mixture

Sources & evidence

ORD record
ord-782d16384ea64d2196a45f567b403df3
Source dataset
uspto-grants-1977_02
Patent number
US04008068

Reaction notes

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