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

HRID 55066

Reaction equation

HRID 55066 reaction equation
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

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 702EthanolSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-ddb4f227ade34c0fa23ac2005f0389d6
Source dataset
uspto-grants-1997_04
Patent number
US05624937

Linked notes

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