N,N-Dimethylaniline → 4-Chloro-2-(methylthio)pyrazolo[1,5-a][1,3,5]triazine

HRID 1896084Notes

Reaction equation

HRID 1896084 reaction equation
CN(C)C1C=CC=CC=1.[CH3:10][S:11][C:12]1[N:17]=[C:16](O)[N:15]2[N:19]=[CH:20][CH:21]=[C:14]2[N:13]=1.P(Cl)(Cl)([Cl:24])=O>>[Cl:24][C:16]1[N:15]2[N:19]=[CH:20][CH:21]=[C:14]2[N:13]=[C:12]([S:11][CH3:10])[N:17]=1

Participants

4

Reactant 3

HCID 949N,N-DimethylanilineHCID 24813Phosphorus oxychlorideHCID 1354442592-(Methylthio)pyrazolo[1,5-a][1,3,5]triazin-4(3H)-one

Product 1

HCID 129161154-Chloro-2-(methylthio)pyrazolo[1,5-a][1,3,5]triazine

Procedure

To a mixture of 10 mL of phosphorus oxychloride and 1 mL of N,N-dimethylaniline was added 0.5 g of 2-(methylthio)pyrazolo[1,5-a][1,3,5]triazin-4-ol (crude from previous step). The solution was refluxed for 30-60 minutes until all the solid dissolved. The excess phosphorus was removed under reduced pressure and the syrupy residue poured with vigorous stirring onto a mixture of ice water. After 10 minutes, the aqueous solution was extracted with ether. The ethereal layers were collected and washed with cold water, then dried with anhydrous Na2SO4. Filtration and concentration under reduced pressure gave the desired 4-chloro-2-(methylthio)pyrazolo[1,5-a][1,3,5]triazine. MS (ES+): 201.0 (M+1)+.

Workup

  1. temperatureThe solution was refluxed for 30-60 minutes until all the solid
  2. dissolutiondissolved
  3. customThe excess phosphorus was removed under reduced pressure
  4. additionthe syrupy residue poured
  5. extractionthe aqueous solution was extracted with ether
  6. customThe ethereal layers were collected
  7. washwashed with cold water
  8. dry with materialdried with anhydrous Na2SO4
  9. filtrationFiltration and concentration under reduced pressure

Sources & evidence

ORD record
ord-188fee9362ee41a1b88b77e68162f576
Source dataset
uspto-grants-2013_08
Patent number
US08518931B2

Reaction notes

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