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

HRID 55064

Reaction equation

HRID 55064 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 moles, 3.0 g), 4-aminothiophenol (15.2 moles, 1.9 g), and DMAP (15.2 moles, 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, 62.82 H, 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-db0649b9e555498e904d0609c1d4c17a
Source dataset
uspto-grants-1997_04
Patent number
US05624937

Linked notes

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