Phosphorus oxychloride → HCID 15017543, compound

HRID 1031375Notes

Reaction equation

HRID 1031375 reaction equation
P(Cl)(Cl)([Cl:3])=O.[F:6][C:7]([F:30])([F:29])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[NH:14][S:15]([C:18]1[N:28]=[C:21]2[N:22]=[C:23]([CH3:27])[CH:24]=[C:25](O)[N:20]2[N:19]=1)(=[O:17])=[O:16]>C(#N)C>[F:6][C:7]([F:30])([F:29])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[NH:14][S:15]([C:18]1[N:28]=[C:21]2[N:22]=[C:23]([CH3:27])[CH:24]=[C:25]([Cl:3])[N:20]2[N:19]=1)(=[O:17])=[O:16]

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178429186HCID 178429186, compound

Product 1

HCID 15017543HCID 15017543, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Phosphorus oxychloride (135 ml, 1.47 mol) was diluted with 335 ml of dry acetonitrile and added to 15 g (40 mmol) of N-(2-trifluoromethylphenyl)-7-hydroxy-5-methyl-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonamide in a one liter flask and heated to reflux with stirring. After about 3 days, the reaction was found to be complete by thin layer chromatography. Volatiles were removed by evaporation under reduced pressure until the mixture became very viscous and the residue was poured onto about one liter of ice and water with stirring. After about 30 minutes, the solid that formed was collected by filtration, washed with ice water, and dried under reduced pressure at room temperature. It was then dissolved in methylene chloride and the resulting solution dried over magnesium sulfate for about five minutes and filtered. The volatiles were removed from the filtrate by evaporation under reduced pressure to obtain the title compound as a white solid residue. The product, the structure of which was confirmed by NMR analysis, amounted to 13.4 g (85.4 percent of theory).

Workup

  1. temperatureheated
  2. temperatureto reflux
  3. customVolatiles were removed by evaporation under reduced pressure until the mixture
  4. additionthe residue was poured onto about one liter of ice and water
  5. stirringwith stirring
  6. waitAfter about 30 minutes
  7. customthe solid that formed
  8. filtrationwas collected by filtration
  9. washwashed with ice water
  10. customdried under reduced pressure at room temperature
  11. dissolutionIt was then dissolved in methylene chloride
  12. dry with materialthe resulting solution dried over magnesium sulfate for about five minutes
  13. filtrationfiltered
  14. customThe volatiles were removed from the filtrate by evaporation under reduced pressure

Sources & evidence

ORD record
ord-19527726a4d64aabb3d069a1549ff6bc
Source dataset
uspto-grants-1990_09
Patent number
US04954163

Reaction notes

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