Acetic Acid → Ethyl 2-(benzylsulfanyl)-7-methyl[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxylate

HRID 477230Notes

Reaction equation

HRID 477230 reaction equation
[NH2:1][C:2]1[N:6]=[C:5]([S:7][CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[NH:4][N:3]=1.C(OC=[CH:19][C:20](=O)[CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])C.[C:28](O)(=O)C>>[CH2:8]([S:7][C:5]1[N:6]=[C:2]2[N:1]=[CH:28][C:21]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[C:20]([CH3:19])[N:3]2[N:4]=1)[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 54463595Ethyl ethoxymethyleneacetoacetateHCID 178509291HCID 178509291, compound

Product 1

HCID 14155094Ethyl 2-(benzylsulfanyl)-7-methyl[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxylateYield 33%

Procedure

A solution of 15 g (73 mmol) of 3-amino-5-benzylthio-1,2,4-triazole and 15.0 g (80.0 mmol) of ethyl ethoxymethyleneacetoacetate in 250 ml of glacial acetic acid was heated at reflux for 60 hours. After cooling the volume of the reaction was reduced to approximately one quarter of the original volume by evaporation at reduced pressure. The resulting residue was poured into water, and the solid which separated was collected by filtration, washed with water and dried to yield 7.88 g (33%) of the desired product as a solid, m.p. 98°-99° C. IR and 1H NMR spectra were in agreement with the assigned structure.

Workup

  1. temperatureat reflux for 60 hours
  2. temperatureAfter cooling the volume of the reaction
  3. customwas reduced to approximately one quarter of the original volume by evaporation at reduced pressure
  4. additionThe resulting residue was poured into water
  5. customthe solid which separated
  6. filtrationwas collected by filtration
  7. washwashed with water
  8. customdried

Sources & evidence

ORD record
ord-943d09d27784469d9f846be6bbedbef5
Source dataset
uspto-grants-1989_12
Patent number
US04886883

Reaction notes

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