Tetrahydrofuran → 2-(4-Aminophenylthio)-4-phenylquinoline

HRID 55066

반응식

HRID 55066 반응식
Cl[C:2]1[CH:11]=[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[NH2:18][C:19]1[CH:24]=[CH:23][C:22]([SH:25])=[CH:21][CH:20]=1.C1COCC1>CN(C1C=CN=CC=1)C.C(O)C>[NH2:18][C:19]1[CH:24]=[CH:23][C:22]([S:25][C:2]2[CH:11]=[C:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[N:3]=2)=[CH:21][CH:20]=1

참가 물질

6

반응물 3

HCID 8028TetrahydrofuranHCID 145104-AminothiophenolHCID 23066872-Chloro-4-phenylquinoline

생성물 1

HCID 189716782-(4-Aminophenylthio)-4-phenylquinoline수율 451.6%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 702Ethanol용매

실험 절차

2-Chloro-4-phenylquinoline (4.18 mmoles, 10.0 g), 4-aminothiophenol (41.8 mmoles, 5.2 g) and DMAP (41.8 mmoles, 5.0 g) were stirred in 200 ml ethanol and 50 ml THF for 3 days. The solution was concentrated, ethyl acetate added, washed with water, dried over sodium sulfate and the solvent removed. The product was purified by HPLC over silica gel eluted with 30% ethyl acetate in hexane to yield 2-(4-aminophenylthio)-4-phenylquinoline 6.2 g, 45%. Mass Spec (FD) 328. Calculated for C21H16N2S: C, 76.80; H, 4.91 N, 8.53. Found: C, 77.04; H, 5.00; N, 8.55.

후처리

  1. concentrationThe solution was concentrated
  2. additionethyl acetate added
  3. washwashed with water
  4. dry with materialdried over sodium sulfate
  5. customthe solvent removed
  6. customThe product was purified by HPLC over silica gel
  7. washeluted with 30% ethyl acetate in hexane

출처 및 근거

ORD 기록
ord-ddb4f227ade34c0fa23ac2005f0389d6
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05624937

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