Phosphorus oxychloride → N-(2,6-dichloro-3-methylphenyl)-7-chloro-5-methyl-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonamide

HRID 1031374Notes

Reaction equation

HRID 1031374 reaction equation
P(Cl)(Cl)([Cl:3])=O.[Cl:6][C:7]1[C:12]([CH3:13])=[CH:11][CH:10]=[C:9]([Cl:14])[C:8]=1[NH:15][S:16]([C:19]1[N:29]=[C:22]2[N:23]=[C:24]([CH3:28])[CH:25]=[C:26](O)[N:21]2[N:20]=1)(=[O:18])=[O:17]>C(#N)C>[Cl:6][C:7]1[C:12]([CH3:13])=[CH:11][CH:10]=[C:9]([Cl:14])[C:8]=1[NH:15][S:16]([C:19]1[N:29]=[C:22]2[N:23]=[C:24]([CH3:28])[CH:25]=[C:26]([Cl:3])[N:21]2[N:20]=1)(=[O:18])=[O:17]

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178429188HCID 178429188, compound

Product 1

HCID 15017542N-(2,6-dichloro-3-methylphenyl)-7-chloro-5-methyl-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonamide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 100 ml of phosphoryl chloride in 400 ml of dry acetonitrile was added to 12.0 g (30.9 mmol) of N-(2,6-dichloro-3-methylphenyl)-7-hydroxy-5-methyl-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonamide and heated to reflux with stirring. After about 24 hours, the mixture became a solution which appeared to contain little or no starting material by thin layer chromatography. The volatiles were largely removed by evaporation under reduced pressure and the residue poured onto about one liter of ice and water with stirring using fresh acetonitrile as a transfer solvent. The solid in the resulting mixture was collected by filtration, washed with water, and dried under reduced pressure at 70° C. overnight. The resulting solid, which was found to be the title compound by NMR analysis, amounted to 8.4 g (67 percent of theory).

Workup

  1. temperatureheated
  2. temperatureto reflux
  3. customThe volatiles were largely removed by evaporation under reduced pressure
  4. additionthe residue poured onto about one liter of ice and water
  5. stirringwith stirring
  6. filtrationThe solid in the resulting mixture was collected by filtration
  7. washwashed with water
  8. customdried under reduced pressure at 70° C. overnight

Sources & evidence

ORD record
ord-60305243cecf44e4be7302169b86ffdb
Source dataset
uspto-grants-1990_09
Patent number
US04954163

Reaction notes

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