3-Chloro-2,4-pentanedione → 2-Benzylthio-6-chloro-5,7-dimethyl-1,2,4-triazolo[1,5-a]pyrimidine

HRID 649446Notes

Reaction equation

HRID 649446 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.[Cl:15][CH:16]([C:20](=O)[CH3:21])[C:17](=O)[CH3:18]>C(O)(=O)C>[CH2:8]([S:7][C:5]1[N:6]=[C:2]2[N:1]=[C:17]([CH3:18])[C:16]([Cl:15])=[C:20]([CH3:21])[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 743283-Chloro-2,4-pentanedioneHCID 178509291HCID 178509291, compound

Product 1

HCID 141550892-Benzylthio-6-chloro-5,7-dimethyl-1,2,4-triazolo[1,5-a]pyrimidineYield 79%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a suspension of 153 g (0.74 mol) 3-amino-5-benzylthio-1,2,4-triazole in 250 ml of glacial acetic acid was added 100 g (0.74 mol) of 3-chloro-2,4-pentanedione in a dropwise manner. The reaction mixture was heated at reflux for 18 hours and cooled to room temperature. The reaction mixture was poured over ice and the oil which separated solidified upon stirring. The solid was collected by filtration and recrystallized from methanol to yield 116 g (79%) of the desired product as an off white solid, m.p. 164°-166° C. IR and 1H NMR spectra were in agreement with the assigned structure.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 18 hours
  3. additionThe reaction mixture was poured over ice
  4. customthe oil which separated
  5. filtrationThe solid was collected by filtration
  6. customrecrystallized from methanol

Sources & evidence

ORD record
ord-75595f79f7da4eb0a3a5c16c378ed1c2
Source dataset
uspto-grants-1988_04
Patent number
US04740233

Reaction notes

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