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

HRID 1721117

반응식

HRID 1721117 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

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 produce 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.

후처리

  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
  11. customto give g, 71%
  12. customof pure produce with mp 257°-258° C

출처 및 근거

ORD 기록
ord-a40c7524c3604558a8e2b15e574ed849
출처 데이터셋
uspto-grants-1996_04
특허 번호
US05508426

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