Water → HCID 68536293, compound

HRID 2389325Notes

Reaction equation

HRID 2389325 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([SH:8])[CH:5]=[CH:6][CH:7]=1.C([O-])([O-])=O.[K+].[K+].CS(O[CH2:20][CH2:21][CH2:22][N:23]1[CH:28]=[C:27]([CH:29]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH:26]=[CH:25][C:24]1=[O:42])(=O)=O.O>CN(C=O)C>[C:30]1([CH:29]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[C:27]2[CH:26]=[CH:25][C:24](=[O:42])[N:23]([CH2:22][CH2:21][CH2:20][S:8][C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([OH:1])[CH:3]=3)[CH:28]=2)[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 27366133-HydroxybenzenethiolHCID 86637899HCID 86637899, compound

Product 1

HCID 68536293HCID 68536293, compoundYield 81.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-hydroxythiophenol (222 mg) in DMF (15 mL) were added K2CO3 (243 mg) and 3-[5-(diphenylmethyl)-2-oxopyridin-1(2H)-yl]propyl methanesulfonate (700 mg) at ambient temperature and the mixture was stirred for 7 hours. Water was added to the mixture at ambient temperature and the resulting mixture was extracted with EtOAc. The organic layer was washed with brine, dried over anhydrous MgSO4, filtered and evaporated in vacuo. The residue was purified by silica gel column chromatography (n-hexane:EtOAc=1:1) to afford 5-(diphenylmethyl)-1-{3-[(3-hydroxyphenyl)sulfanyl]propyl}pyridin-2(1H)-one (610 mg) as a colorless oil.

Workup

  1. extractionthe resulting mixture was extracted with EtOAc
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous MgSO4
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customThe residue was purified by silica gel column chromatography (n-hexane:EtOAc=1:1)

Sources & evidence

ORD record
ord-8a285983ceec4314b247148a3e6515ec
Source dataset
uspto-grants-2012_09
Patent number
US08273745B2

Reaction notes

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