Hydrochloric Acid → N-(2-benzoyl-4-chloro-phenyl)-4-cyano-benzenesulfonamide

HRID 18897

反応式

HRID 18897 の反応式
[NH2:1][C:2]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:5].[C:17]([C:19]1[CH:24]=[CH:23][C:22]([S:25](Cl)(=[O:27])=[O:26])=[CH:21][CH:20]=1)#[N:18].Cl>N1C=CC=CC=1.CC(C)=O.O>[C:4]([C:3]1[CH:12]=[C:13]([Cl:16])[CH:14]=[CH:15][C:2]=1[NH:1][S:25]([C:22]1[CH:21]=[CH:20][C:19]([C:17]#[N:18])=[CH:24][CH:23]=1)(=[O:27])=[O:26])(=[O:5])[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

参加物

7

反応物 3

HCID 313Hydrochloric AcidHCID 128702-Amino-5-chlorobenzophenoneHCID 394974-Cyanobenzenesulfonyl chloride

生成物 1

HCID 10408471N-(2-benzoyl-4-chloro-phenyl)-4-cyano-benzenesulfonamide収率 114%

試薬・触媒・溶媒 3

HCID 180Acetone溶媒2 回HCID 962Water溶媒HCID 1049Pyridine溶媒2 回

実験手順

2-Amino-5-chlorobenzophenone (2.92 g, 12.60 mmol) was dissolved in 60 mL of pyridine and 4-cyanobenzenesulfonyl chloride (2.66 g, 13.2 mmol) in 10 mL pyridine was then added. The mixture was stirred overnight at room temperature under N2, then poured in a steady stream into 350 mL vigorously stirring chilled 6M HCl which resulted in the precipitation of a yellow solid which was collected by vacuum filtration, washed well with H2O, then dissolved in 50 mL EtOAc and the solvents removed under vacuum to get a reddish powder which was dissolved in 75 mL boiling acetone. 150 mL of H2O was added in a slow stream to the hot, stirring acetone solution. A yellow precipitate formed upon cooling which was collected by vacuum filtration and dried overnight under vacuum to get 5.7 g product as a reddish powder (quant). 1H NMR (DMSO) δ 10.28 (s, 1H) 7.92 (dd, J=1.6, 8.8, 2H) 7.70 (d, 2H) 7.64(t, 1H) 7.58-7.52 (m, 3H) 7.50-7.46 (m, 2H) 7.42 (d, J=2.8 Hz, 1H) 7.03 (d, 8.8 Hz, 1H). MS: m/z =397.0 (M++1).

後処理

  1. additionpoured in a steady stream into 350 mL
  2. stirringvigorously stirring
  3. customresulted in the precipitation of a yellow solid which
  4. filtrationwas collected by vacuum filtration
  5. washwashed well with H2O
  6. dissolutiondissolved in 50 mL EtOAc
  7. customthe solvents removed under vacuum
  8. customto get a reddish powder which
  9. dissolutionwas dissolved in 75 mL
  10. customA yellow precipitate formed
  11. temperatureupon cooling which
  12. filtrationwas collected by vacuum filtration
  13. customdried overnight under vacuum

出典と根拠

ORDレコード
ord-31d04f027d8749beab6c7f25aa16bff1
出典データセット
uspto-grants-2010_06
特許番号
US07741519B2

関連ノート

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