4-Aminothiophenol → 2-(4-Aminophenylthio)-6-chloroquinoline

HRID 2395320Notes

Reaction equation

HRID 2395320 reaction equation
Cl[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([Cl:12])[CH:8]=2)[N:3]=1.[NH2:13][C:14]1[CH:19]=[CH:18][C:17]([SH:20])=[CH:16][CH:15]=1>CN(C1C=CN=CC=1)C>[NH2:13][C:14]1[CH:19]=[CH:18][C:17]([S:20][C:2]2[CH:11]=[CH:10][C:9]3[C:4](=[CH:5][CH:6]=[C:7]([Cl:12])[CH:8]=3)[N:3]=2)=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 145104-AminothiophenolHCID 6075022,6-Dichloroquinoline

Product 1

HCID 189716572-(4-Aminophenylthio)-6-chloroquinolineYield 19%

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

2,6-Dichloroquinoline (15.2 mmoles, 3.0 g), 4-aminothiophenol (15.2 mmoles, 1.9 g), and DMAP 15.2 mmoles, 1.85 g) were stirred at room temperature for 3 days. The solvent was removed, diluted with ethyl acetate, washed with water, dried over sodium sulfate and concentrated. The product was purified by HPLC over silica gel eluted with 25% ethyl acetate in hexane to yield 2-(4-aminophenylthio)-6-chloroquinoline 830 mg, 19%. Mass spec (FD) 286. Calculated. for C15H11ClN2S: C, 62.82H, 3.87; N, 9.77. Found: C, 63.09; H, 3.94; N, 9.61.

Workup

  1. customThe solvent was removed
  2. additiondiluted with ethyl acetate
  3. washwashed with water
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customThe product was purified by HPLC over silica gel
  7. washeluted with 25% ethyl acetate in hexane

Sources & evidence

ORD record
ord-b24847c6d67a4ae399016ee9a2ef96e4
Source dataset
uspto-grants-1998_09
Patent number
US05814646

Reaction notes

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