Hydrochloric Acid → 5-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylic acid

HRID 1679681Notes

Reaction equation

HRID 1679681 reaction equation
[O:1]=[C:2]1[N:7]2[CH:8]=[CH:9][S:10][C:6]2=[N:5][CH:4]=[C:3]1[C:11]([O:13]CC)=[O:12].Cl>>[O:1]=[C:2]1[N:7]2[CH:8]=[CH:9][S:10][C:6]2=[N:5][CH:4]=[C:3]1[C:11]([OH:13])=[O:12]

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 838816ethyl 5-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate

Product 1

HCID 7623625-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylic acid

Procedure

A mixture of ethyl 5-oxo-5H-thiazolo[3,2-a]pyrimidine-6-carboxylate (11.2g., 50mM) and 2N hydrochloric acid (75ml) was heated under reflux for 5 hours. The reaction mixture was cooled and filtered to give the required product in 79.7% weight yield (7.81g). νmax (KBr disc) 1720 (acid C=O)cm-1 ; λmax (NaHCO3 solution) 232nm (εm 2650), 263nm (εm 2030), 328nm (εm 6000) and 339nm (εm 5400); (Found: C, 43,65; H, 2.26; N, 14.16; S, 16.62%. C7H4N2O3S requires C, 43.87; H, 2.06; N, 14.28; S, 16.32%.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 5 hours
  3. temperatureThe reaction mixture was cooled
  4. filtrationfiltered

Sources & evidence

ORD record
ord-1c161a0b3676431084655a0a6c625adc
Source dataset
uspto-grants-1978_03
Patent number
US04081545

Reaction notes

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