4,4-Dimethoxy-2-butanone → 2-Benzylthio-7-methyl-1,2,4-triazolo[1,5-a]pyrimidine

HRID 844960Notes

Reaction equation

HRID 844960 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.CO[CH:17](OC)[CH2:18][C:19](=O)[CH3:20]>C(O)(=O)C>[CH2:8]([S:7][C:5]1[N:6]=[C:2]2[N:1]=[CH:17][CH:18]=[C:19]([CH3:20])[N:3]2[N:4]=1)[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 2285484,4-Dimethoxy-2-butanoneHCID 178509291HCID 178509291, compound

Product 1

HCID 141550872-Benzylthio-7-methyl-1,2,4-triazolo[1,5-a]pyrimidineYield 43.9%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Conditions

Temperature
100 °C

Procedure

A solution of 50 g (0.24 mol) of 3-amino-5-benzylthio-1,2,4-triazole in 500 ml of glacial acetic acid was added dropwise over 3-4 hours to a solution of 34.0 g (0.25 mol) of acetylacetaldehyde dimethyl acetal in 500 ml of glacial acetic acid heated at 100° C. After the addition was complete the reaction mixture was heated at reflux overnight, cooled to room temperature and poured into an ice-water mixture. The solid which separated was collected by filtration and recrystallized from ethanol to yield 27 g (41%) of the desired product as a solid, m.p. 102°-104° C. IR and 1H NMR spectra were in agreement with the assigned structure.

Workup

  1. additionAfter the addition
  2. temperaturewas heated
  3. temperatureat reflux overnight
  4. temperaturecooled to room temperature
  5. customThe solid which separated
  6. filtrationwas collected by filtration
  7. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-92b6a96276f448da894c0d90cafedc79
Source dataset
uspto-grants-1988_07
Patent number
US04755212

Reaction notes

Loading…