Thionyl Chloride → HCID 86739760, compound

HRID 1979748Notes

Reaction equation

HRID 1979748 reaction equation
[C:1]1([N:7]2[N:11]3[C:12](=[O:19])[C:13]([C:16]([OH:18])=[O:17])=[CH:14][N:15]=[C:10]3[CH:9]=[CH:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S(Cl)(Cl)=O.O1[CH2:29][CH2:28]OCC1>>[C:1]1([N:7]2[N:11]3[C:12](=[O:19])[C:13]([C:16]([O:18][CH2:2][CH2:1][N:7]([CH2:28][CH3:29])[CH2:8][CH3:9])=[O:17])=[CH:14][N:15]=[C:10]3[CH:9]=[CH:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 3

HCID 24386Thionyl ChlorideHCID 312751,4-DioxaneHCID 13216596HCID 13216596, compound

Product 1

HCID 86739760HCID 86739760, compound

Procedure

1-phenyl-7-oxo-1H,7H-pyrazolo[1,5-a]pyrimidine-6-carboxylic acid (1.2 g) was reacted with thionyl chloride (0.8 ml) in dioxane (30 ml) at the reflux temperature for 3 hours, then the mixture was evaporated in vacuo to dryness. The residue was dissolved in dioxane (30 ml) and reacted with 2-(diethylamino)-ethanol (1.2 g) at room temperature for 24 hours. After dilution with water and alkalinization with Na2CO3 the precipitate was extracted with ethyl acetate: evaporation to dryness and crystallization from chloroformethanol gave 0.7 g of 1-phenyl-7-oxo-1H,7H-pyrazolo[1,5-a]pyrimidine-6-carboxylic acid, 2-(diethylamino)-ethyl ester, m.p. 127°-130° C.

Workup

  1. customthe mixture was evaporated in vacuo to dryness
  2. dissolutionThe residue was dissolved in dioxane (30 ml)
  3. customreacted with 2-(diethylamino)-ethanol (1.2 g) at room temperature for 24 hours
  4. extractionAfter dilution with water and alkalinization with Na2CO3 the precipitate was extracted with ethyl acetate
  5. customevaporation
  6. customto dryness and crystallization from chloroformethanol

Sources & evidence

ORD record
ord-773d79c80c19486da0a0e7812e7b72f2
Source dataset
uspto-grants-1984_11
Patent number
US04482555

Reaction notes

Loading…