Hexafluoroacetylacetone → 2-Benzylthio-5,7-bis-(trifluoromethyl)-1,2,4-triazolo[1,5-a]pyrimidine

HRID 477231Notes

Reaction equation

HRID 477231 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3](=O)[CH2:4][C:5](=O)[C:6]([F:9])([F:8])[F:7].[NH2:14][C:15]1[N:19]=[C:18]([S:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[NH:17][N:16]=1>C(O)(=O)C>[CH2:21]([S:20][C:18]1[N:19]=[C:15]2[N:14]=[C:5]([C:6]([F:9])([F:8])[F:7])[CH:4]=[C:3]([C:2]([F:13])([F:12])[F:1])[N:16]2[N:17]=1)[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

4

Reactant 2

HCID 73706HexafluoroacetylacetoneHCID 178509291HCID 178509291, compound

Product 1

HCID 141550962-Benzylthio-5,7-bis-(trifluoromethyl)-1,2,4-triazolo[1,5-a]pyrimidineYield 94%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 20.8 g (0.100 mol) of 1,1,1,5,5,5-hexafluoro-2,4-pentanedione and 20.6 g (0.100 mol) of 3-amino-5-benzylthio-1,2,4-triazole in 150 ml of glacial acetic acid was heated at reflux for 14 hours. The solution was cooled to room temperature and poured over ice. The solid which separated was collected by filtration, washed with water and dried in vacuo to yield 35.5 g (94%) of the desired product as a pale yellow solid, m.p. 78.5°-80.5° C. IR, 1H NMR and 19F NMR spectra were in agreement with the assigned structure.

Workup

  1. temperatureat reflux for 14 hours
  2. additionpoured over ice
  3. customThe solid which separated
  4. filtrationwas collected by filtration
  5. washwashed with water
  6. customdried in vacuo

Sources & evidence

ORD record
ord-a54fb3ba1864437886df2c99e70f2b4b
Source dataset
uspto-grants-1989_12
Patent number
US04886883

Reaction notes

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