Chloroform → 3-Chloro-7-(alpha,alpha,alpha-trifluoro-m-tolyl)pyrazolo[1,5-a]pyrimidine

HRID 1447855Notes

Reaction equation

HRID 1447855 reaction equation
[Cl:1]N1C2C=CC=CC=2N=N1.[F:11][C:12]([F:29])([F:28])[C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([C:19]2[N:24]3[N:25]=[CH:26][CH:27]=[C:23]3[N:22]=[CH:21][CH:20]=2)[CH:14]=1.C(Cl)(Cl)Cl.[OH-].[Na+]>C(Cl)Cl>[Cl:1][C:27]1[CH:26]=[N:25][N:24]2[C:19]([C:15]3[CH:14]=[C:13]([C:12]([F:28])([F:11])[F:29])[CH:18]=[CH:17][CH:16]=3)=[CH:20][CH:21]=[N:22][C:23]=12

Participants

6

Reactant 4

HCID 6212ChloroformHCID 14798Sodium HydroxideHCID 887611-ChlorobenzotriazoleHCID 197562037-[3-(Trifluoromethyl)phenyl]pyrazolo[1,5-a]pyrimidine

Product 1

HCID 197562203-Chloro-7-(alpha,alpha,alpha-trifluoro-m-tolyl)pyrazolo[1,5-a]pyrimidine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 3.3 g. portion of N-chlorobenzotriazole is added to a solution of 5.26 g. of 7-(α,α,α-trifluoro-m-tolyl)pyrazolo[1,5-a]pyrimidine in 50 ml. of chloroform producing an exothermic reaction. The mixture is refluxed on a steam bath for 15 minutes, cooled to room temperature and then poured into an ice-cold solution of 2.5 N sodium hydroxide. The organic layer is separated, dried over sodium sulfate and passed through a hydrous magnesium silicate column. The effluent is heated to reflux and hexane is added giving a solid. The solid is dissolved in methylene chloride re-processed through the column and precipitated from refluxing solution with hexane giving crystals of the desired product, m.p. 155°-157° C.

Workup

  1. temperatureThe mixture is refluxed on a steam bath for 15 minutes
  2. customThe organic layer is separated
  3. dry with materialdried over sodium sulfate
  4. temperatureThe effluent is heated
  5. temperatureto reflux
  6. additionhexane is added
  7. customgiving a solid
  8. customprecipitated
  9. temperaturefrom refluxing solution with hexane giving crystals of the desired product, m.p. 155°-157° C.

Sources & evidence

ORD record
ord-07ab0058a0b04bc39cffc3c93d675cc6
Source dataset
uspto-grants-1979_12
Patent number
US04178449

Reaction notes

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