Water → 2-Benzylthio-5-fluoromethyl-7-chloro-1,2,4-triazolo[1,5-a]pyrimidine

HRID 1199892Notes

Reaction equation

HRID 1199892 reaction equation
[CH2:1]([S:8][C:9]1[N:20]=[C:12]2[N:13]=[C:14]([CH2:18][F:19])[CH:15]=[C:16](O)[N:11]2[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.P(Cl)(Cl)([Cl:23])=O.O>C(Cl)Cl.CCCCCC>[CH2:1]([S:8][C:9]1[N:20]=[C:12]2[N:13]=[C:14]([CH2:18][F:19])[CH:15]=[C:16]([Cl:23])[N:11]2[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 962WaterHCID 24813Phosphorus oxychlorideHCID 178516166HCID 178516166, compound

Product 1

HCID 146234712-Benzylthio-5-fluoromethyl-7-chloro-1,2,4-triazolo[1,5-a]pyrimidine

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8058HexaneSolvent

Procedure

A mixture of 17.0 g (58.6 mmol) of 2-benzylthio-5-fluoromethyl-7-hydroxy-1,2,4-triazolo[1,5-a]pyrimidine and 100 ml of phosphorus oxychloride was heated at reflux for three hours and was then concentrated by simple distillation using a water aspirator to reduce the pressure to obtain a dark, viscous oil. This was dissolved in 300 ml of methylene chloride and treated cautiously with stirring with 200 ml of water. The mixture was stirred vigorously for 30 min. at ambient temperature and then allowed to separate into phases. The organic phase was separated, washed with water and saturated aqueous sodium bicarbonate, dried over magnesium sulfate, and concentrated by evaporation under reduced pressure to obtain a dark oil. This solidified on trituration in hexane containing a little methylene chloride to yield 12.2 g (67 percent of theory) of the title compound as a tan solid melting at 81°-86° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for three hours
  3. concentrationwas then concentrated by simple distillation
  4. customto obtain a dark, viscous oil
  5. additiontreated cautiously
  6. customto separate into phases
  7. customThe organic phase was separated
  8. washwashed with water and saturated aqueous sodium bicarbonate
  9. dry with materialdried over magnesium sulfate
  10. concentrationconcentrated by evaporation under reduced pressure
  11. customto obtain a dark oil

Sources & evidence

ORD record
ord-acacb6b3403348288e439f9b457c9fb2
Source dataset
uspto-grants-1990_02
Patent number
US04904301

Reaction notes

Loading…