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

HRID 1636087ノート

反応式

HRID 1636087 の反応式
[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

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 962Water溶媒

反応条件

温度
100 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-384ee184fd234ee18ee4db7bd999d5ae
出典データセット
uspto-grants-2003_01
特許番号
US06512121B2

反応ノート

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