Phosphorus oxychloride → HCID 21255050, compound

HRID 636449Notes

Reaction equation

HRID 636449 reaction equation
[C:1]1([S:7]([C:10]2[C:11]([S:24][CH3:25])=[N:12][N:13]3[C:18](O)=[CH:17][C:16]([CH2:20][N:21]([CH3:23])[CH3:22])=[N:15][C:14]=23)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O=P(Cl)(Cl)[Cl:28]>>[C:1]1([S:7]([C:10]2[C:11]([S:24][CH3:25])=[N:12][N:13]3[C:18]([Cl:28])=[CH:17][C:16]([CH2:20][N:21]([CH3:23])[CH3:22])=[N:15][C:14]=23)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178503608HCID 178503608, compound

Product 1

HCID 21255050HCID 21255050, compoundYield 88%

Procedure

A suspension of 1.3 g (3.43 mmol) of 3-benzenesulphonyl-5-dimethylaminomethyl-2-methylsulphanyl-pyrazolo[1,5-a]pyrimidin-7-ol in 50 ml of POCl3 was heated at reflux for 3 hrs. The reaction solution was cooled to RT and evaporated. The residue was treated with 100 ml of ice-water and the pH value of the solution was adjusted to 8 with sat. NaHCO3 solution. The aqueous phase was extracted three times with 100 ml of CH2Cl2 and the organic phases were dried (MgSO4), filtered and evaporated. Chromatography (SiO2, CH2Cl2/AcOEt 1:1) of the residue yielded 1.2 g (88%) of (3-benzenesulphonyl-7-chloro-2-methylsulphanyl-pyrazolo[1,5-a]pyrimidin-5-ylmethyl)-dimethyl-amine as a colorless foam.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 3 hrs
  3. customevaporated
  4. additionThe residue was treated with 100 ml of ice-water
  5. extractionThe aqueous phase was extracted three times with 100 ml of CH2Cl2
  6. dry with materialthe organic phases were dried (MgSO4)
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-667d2d018d184736a8f23aaa7895fecc
Source dataset
uspto-grants-2001_02
Patent number
US06194410B1

Reaction notes

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