Phosphorus oxychloride → HCID 14152228, compound

HRID 569700Notes

Reaction equation

HRID 569700 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[NH:9][S:10]([C:13]1[N:23]=[C:16]2[N:17]=[C:18]([CH3:22])[CH:19]=[C:20](O)[N:15]2[N:14]=1)(=[O:12])=[O:11].P(Cl)(Cl)([Cl:26])=O>C(#N)C>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[NH:9][S:10]([C:13]1[N:23]=[C:16]2[N:17]=[C:18]([CH3:22])[CH:19]=[C:20]([Cl:26])[N:15]2[N:14]=1)(=[O:12])=[O:11]

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178429187HCID 178429187, compound

Product 1

HCID 14152228HCID 14152228, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A suspension of 10.0 g (27.0 mmol) of N-(2,6-dichlorophenyl)-7-hydroxy-5-methyl-1,2,4-triazolo-[1,5-a]-pyrimidine-2-sulfonamide and 100 ml (1.1 mol) of phosphorous oxychloride in 700 ml of acetonitrile (dried over 4A Molecular Sieves) was heated at reflux for 24 hr. As the reaction progressed the mixture became homogeneous. After cooling the solution was concentrated by rotary evaporation in vacuo and the resulting residue was diluted with 300 ml of methylene chloride and 10 ml of water. The methylene chloride solution was decanted off and the solid that had formed was triturated with 100 ml of hexane and 5 ml of water. The resulting yellow solid was collected. Recovered 9.0 g (85 percent) of the desired product; mp 217°-220° C. An analytical sample could be prepared by recrystallization from methanol (mp 218°-221° C.).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 24 hr
  3. temperatureAfter cooling the solution
  4. concentrationwas concentrated by rotary evaporation in vacuo
  5. additionthe resulting residue was diluted with 300 ml of methylene chloride and 10 ml of water
  6. customThe methylene chloride solution was decanted off
  7. customthe solid that had formed
  8. customwas triturated with 100 ml of hexane and 5 ml of water
  9. customThe resulting yellow solid was collected
  10. customRecovered 9.0 g (85 percent) of the desired product
  11. customAn analytical sample could be prepared by recrystallization from methanol (mp 218°-221° C.)

Sources & evidence

ORD record
ord-bac000d8b10c40b1a0676ed923a26076
Source dataset
uspto-grants-1988_03
Patent number
US04734123

Reaction notes

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