Thiophenol → HCID 9956010, compound

HRID 1082116Notes

Reaction equation

HRID 1082116 reaction equation
[C:1]1([SH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[O:10]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[N:12]=[C:11]1[N:19]([CH2:21][CH2:22][O:23][C:24]1[CH:29]=[CH:28][C:27]([CH2:30][CH:31](Br)[C:32]([O:34][CH3:35])=[O:33])=[CH:26][CH:25]=1)[CH3:20]>CN(C)C=O.O>[O:10]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[N:12]=[C:11]1[N:19]([CH2:21][CH2:22][O:23][C:24]1[CH:25]=[CH:26][C:27]([CH2:30][CH:31]([S:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[C:32]([O:34][CH3:35])=[O:33])=[CH:28][CH:29]=1)[CH3:20]

Participants

6

Reactant 3

HCID 7969ThiophenolHCID 24758Sodium hydrideHCID 23362208HCID 23362208, compound

Product 1

HCID 9956010HCID 9956010, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

Thiophenol (0.92 mL) was added slowly to an ice-cooled, stirred suspension of sodium hydride (60% dispersion in oil, 0.38 g) in dry N,N-dimethylformamide (60 mL). The mixture was allowed to warm to room temperature over 30 minutes prior to the addition of a solution of methyl 3-[4-[2-[N-(2-benzoxazolyl)-N-methylamino]ethoxy]phenyl]-2-bromopropanoate (3.85 g) in N,N-dimethylformamide (40 mL) and the mixture was then heated at 80° C. for 72 hrs, cooled and diluted with water (1 L). The mixture was extracted with ethyl acetate (3×250 mL) and the combined organic solutions washed with water (3×1 L) and brine (1 L), dried (MgSO4) and evaporated. The residue was chromatographed on silica gel using a gradient of 1% methanol to 2% methanol in dichloromethane as eluent to afford the title compound, mp 78°-9° C. (dichloromethane-hexane).

Workup

  1. temperaturecooled
  2. temperaturethe mixture was then heated at 80° C. for 72 hrs
  3. temperaturecooled
  4. extractionThe mixture was extracted with ethyl acetate (3×250 mL)
  5. washthe combined organic solutions washed with water (3×1 L) and brine (1 L)
  6. dry with materialdried (MgSO4)
  7. customevaporated
  8. customThe residue was chromatographed on silica gel using a gradient of 1% methanol to 2% methanol in dichloromethane as eluent

Sources & evidence

ORD record
ord-dd7cbdb9d1044486b5879aa2e1934b90
Source dataset
uspto-grants-1996_12
Patent number
US05589492

Reaction notes

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