Water → HCID 68899031, compound

HRID 735321Notes

Reaction equation

HRID 735321 reaction equation
[SH:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4][OH:5].Cl[C:11]1[CH:20]=[CH:19][C:18]2[C:13](=[CH:14][CH:15]=[C:16]([Cl:21])[CH:17]=2)[N:12]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[Cl:21][C:16]1[CH:17]=[C:18]2[C:13](=[CH:14][CH:15]=1)[N:12]=[C:11]([S:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4][OH:5])[CH:20]=[CH:19]2

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 1382782-MercaptobenzenemethanolHCID 6075022,6-Dichloroquinoline

Product 1

HCID 68899031HCID 68899031, compoundYield 9.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-mercaptobenzyl alcohol (1.78 g, 12.7 mmol), 2,6-dichloroquinoline (2.48 g, 12.5 mmol) and potassium carbonate (1.73 g, 12.5 mmol) in N,N-dimethylformamide (25 mL) was stirred at room temperature under nitrogen for 3 hours, then at 60° C. for 17 hours. The cooled reaction mixture was poured into water and extracted with ethyl acetate (x2). The combined organic layers were washed with brine, dried over MgSO4 and evaporated. The residue was purified by flash column chromatography on silica, eluting with 5-10% ethyl acetate/dichloromethane, to give {2-[(6-chloroquinolin-2-yl)thio]phenyl}methanol (0.37 g, 9%) as a colourless oil. 1H NMR (400 MHz, CDCl3) δ 7.84 (1H, d, J=8.7 Hz), 7.72-7.66 (4H, m), 7.55-7.51 (2H, m), 7.39-7.35 (1H, m), 7.19 (1H, dd, J=1.2, 8.7 Hz), 4.84 (2H, s), 3.78 (1H, s); m/z (ES+) 302, 304 [MH+].

Workup

  1. waitat 60° C. for 17 hours
  2. customThe cooled reaction mixture
  3. extractionextracted with ethyl acetate (x2)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over MgSO4
  6. customevaporated
  7. customThe residue was purified by flash column chromatography on silica
  8. washeluting with 5-10% ethyl acetate/dichloromethane

Sources & evidence

ORD record
ord-84c21f5e2ef64197b0d64e4ec0744d52
Source dataset
uspto-grants-2009_09
Patent number
US07592456B2

Reaction notes

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