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

HRID 2395322Notes

Reaction equation

HRID 2395322 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, 4.91N, 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-9e34b9533c9b498faec1d6283cca03f7
Source dataset
uspto-grants-1998_09
Patent number
US05814646

Reaction notes

Loading…