Sodium Cyanide → 4-[5-(4-Chloro-phenyl)-3-cyanomethyl-pyrazol-1-yl]-benzenesulfonamide

HRID 1057792Notes

Reaction equation

HRID 1057792 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([C:13]3[CH:18]=[CH:17][C:16]([S:19]([NH2:22])(=[O:21])=[O:20])=[CH:15][CH:14]=3)[N:11]=[C:10]([CH2:23]Cl)[CH:9]=2)=[CH:4][CH:3]=1.[C-:25]#[N:26].[Na+]>CS(C)=O.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:12]([C:13]3[CH:14]=[CH:15][C:16]([S:19]([NH2:22])(=[O:20])=[O:21])=[CH:17][CH:18]=3)[N:11]=[C:10]([CH2:23][C:25]#[N:26])[CH:9]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 8929Sodium CyanideHCID 99701264-(5-(4-chlorophenyl)-3-chloromethyl-1H-pyrazol-1-yl]benzenesulfonamide

Product 1

HCID 108331274-[5-(4-Chloro-phenyl)-3-cyanomethyl-pyrazol-1-yl]-benzenesulfonamideYield 75%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A solution of 4-[5-(4-chlorophenyl)-3-chloromethyl-1H-pyrazol-1-yl]benzenesulfonamide from step 1 (350 mg, 0.9 mmol) and sodium cyanide (200 mg), dissolved in 15 mL of dimethylsulfoxide, was warmed to 100° C. for 4 hours. The solution was cooled to room temperature, diluted with water and extracted with ethyl acetate. The ethyl acetate extracts were combined and washed with water, dried over anhydrous MgSO4, filtered and concentrated in vacuo. The residue was purified by flash chromatography over silica gel eluting with 1:1 (v:v) hexane/ethyl acetate. The appropriate fractions were combined and concentrated, and the residue crystallized from ethanol/water to give 4-[5-(4-chlorophenyl)-3-cyanomethyl-1-H-pyrazol-1-yl]benzenesulfonamide as a white solid (251 mg, 75%): mp 212-214° C. Anal. Calc'd. for C17H13ClN4O2S1: C, 54.77; H, 3.51; N, 15.03. Found: C, 54.94; H, 3.61; N, 14.88.

Workup

  1. temperatureThe solution was cooled to room temperature
  2. extractionextracted with ethyl acetate
  3. washwashed with water
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash chromatography over silica gel eluting with 1:1 (v:v) hexane/ethyl acetate
  8. concentrationconcentrated
  9. customthe residue crystallized from ethanol/water

Sources & evidence

ORD record
ord-ef2d8c95ec9b4733927cb781f5e91cb2
Source dataset
uspto-grants-2003_02
Patent number
US06515014B2

Reaction notes

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