4-Hydrazinylbenzenesulfonamide hydrochloride → 4,5-dihydro-4-[3-(trifluoromethyl)-1H-benz[g]indazol-1-yl]benzenesulfonamide

HRID 440067

反応式

HRID 440067 の反応式
[F:1][C:2]([F:17])([F:16])[C:3]([CH:5]1[CH2:14][CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]1=O)=O.[CH:18]1[C:23]([NH:24][NH2:25])=[CH:22][CH:21]=[C:20]([S:26]([NH2:29])(=[O:28])=[O:27])[CH:19]=1.Cl>C(O)C>[F:1][C:2]([F:17])([F:16])[C:3]1[C:5]2[C:6](=[C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][C:12]3=[CH:13][CH:14]=2)[N:24]([CH:23]2[CH2:22][CH:21]=[C:20]([S:26]([NH2:29])(=[O:28])=[O:27])[CH:19]=[CH:18]2)[N:25]=1

参加物

4

反応物 2

HCID 27945674-Hydrazinylbenzenesulfonamide hydrochlorideHCID 69171222-Trifluoroacetyl-1-tetralone

生成物 1

HCID 189203554,5-dihydro-4-[3-(trifluoromethyl)-1H-benz[g]indazol-1-yl]benzenesulfonamide収率 71%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

A 100 mL one necked round bottomed flask equipped with reflux condenser, nitrogen inlet and provisions for magnetic stirring was charged with 2-trifluoroacetyl-1-tetralone (1.21 g, 5.0 mmol), 4-sulfonamido phenylhydrazine hydrochloride (1.12 g, 5.0 mmol) and 25 mL of absolute ethanol. The solution was then warmed to reflux for 15 h and then concentrated in vacuo. The residue was dissolved in ethyl acetate and then washed with water, brine, dried over anhyd. MgSO4, filtered and concentrated in vacuo. The residue was recrystallized from a mixture of ethyl acetate and isooctane to give g, 71% of pure product with mp 257°-258° C. 1H NMR (CDCl3 /CD3OD, 4:1) δ2.7 (m, 2H), 2.9 (m, 2H), 6.6 (m, 1H), 6.9 (m, 1H), 7.1 (m, 1H), 7.16 (m, 1H), 7.53 (m, 2H), 7.92 (m, 2H); 19 F NMR CDCl3 δ-62.5. FAB-MS M+H=394.

後処理

  1. temperaturewith reflux condenser, nitrogen inlet
  2. temperatureThe solution was then warmed
  3. temperatureto reflux for 15 h
  4. concentrationconcentrated in vacuo
  5. dissolutionThe residue was dissolved in ethyl acetate
  6. washwashed with water, brine
  7. customdried over anhyd
  8. filtrationMgSO4, filtered
  9. concentrationconcentrated in vacuo
  10. customThe residue was recrystallized from a mixture of ethyl acetate and isooctane

出典と根拠

ORDレコード
ord-7b8a26dc3fc24ad4a71722d4a399055b
出典データセット
uspto-grants-1996_05
特許番号
US05516907

関連ノート

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