Sulfuryl chloride → HCID 53854580, compound

HRID 1196498Notes

Reaction equation

HRID 1196498 reaction equation
[CH2:1]([O:3][C:4](=[O:22])[CH2:5][C:6]1[C:7]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=2)=[N:8][N:9]2[CH:14]=[CH:13][CH:12]=[N:11][C:10]=12)[CH3:2].S(Cl)([Cl:26])(=O)=O>C(Cl)Cl>[CH2:1]([O:3][C:4](=[O:22])[CH2:5][C:6]1[C:7]([C:15]2[CH:16]=[CH:17][C:18]([Cl:21])=[CH:19][CH:20]=2)=[N:8][N:9]2[CH:14]=[C:13]([Cl:26])[CH:12]=[N:11][C:10]=12)[CH3:2]

Participants

4

Reactant 2

HCID 24648Sulfuryl chlorideHCID 54018450HCID 54018450, compound

Product 1

HCID 53854580HCID 53854580, compoundYield 37.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 3.2 g (0.01 mole) of 2(4-chlorophenyl)pyrazolo[1,5-a]pyrimidine-3-acetic acid ethyl ester in 30 ml of methylene chloride was stirred under nitrogen and cooled to 0° C. in an ice bath. The cooled reaction solution was treated with 1.4 g (0.84 ml) (0.01 mole) of sulfuryl chloride and the reaction was allowed to warm to room temperature. The reaction mixture was concentrated in vacuo and the residue dissolved in 20 ml of methylene chloride, and washed successively with water, saturated sodium carbonate solution, and water, and then concentrated in vacuo to obtain 3.5 of residue. The crude residue was placed on on a 100 g silica gel column and chromatographed with a methanol:benzene gradient (0-4%). Concentration of combined fractions yielded a solid which was recrystallized from benzene (300 mg). A second crop obtained after adding ligroin amounted to 1.1 g of mixed product. The combined residues recrystallized from ethanol to yield 1.3 g (37%) of long pale yellow needles, mp 139°-140° C.

Workup

  1. customThe cooled reaction solution
  2. temperatureto warm to room temperature
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. dissolutionthe residue dissolved in 20 ml of methylene chloride
  5. washwashed successively with water, saturated sodium carbonate solution, and water
  6. concentrationconcentrated in vacuo
  7. customto obtain 3.5 of residue
  8. customchromatographed with a methanol
  9. customConcentration of combined fractions yielded a solid which
  10. customwas recrystallized from benzene (300 mg)
  11. customA second crop obtained
  12. customThe combined residues recrystallized from ethanol

Sources & evidence

ORD record
ord-7bfc16c4866b4db7b74dddb0e5bdef62
Source dataset
uspto-grants-1992_05
Patent number
US05114944

Reaction notes

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