Sodium hydride → HCID 67051248, compound

HRID 1175513Notes

Reaction equation

HRID 1175513 reaction equation
[H-].[Na+].FC1C(F)=CC=CC=1[CH2:11][S:12]([C:15]1[N:20]=[C:19]([N:21]([CH2:29][C:30]2[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[CH:32][CH:31]=2)[S:22]([N:25]2[CH2:28][CH2:27][CH2:26]2)(=[O:24])=[O:23])[CH:18]=[C:17]([O:38][CH3:39])[N:16]=1)(=O)=O.[CH:40]1[CH:45]=[CH:44][C:43]([CH2:46]CS)=[CH:42][CH:41]=1>CN(C=O)C.CCOC(C)=O>[CH3:37][O:36][C:33]1[CH:32]=[CH:31][C:30]([CH2:29][N:21]([C:19]2[CH:18]=[C:17]([O:38][CH3:39])[N:16]=[C:15]([S:12][CH2:11][CH2:46][C:43]3[CH:44]=[CH:45][CH:40]=[CH:41][CH:42]=3)[N:20]=2)[S:22]([N:25]2[CH2:28][CH2:27][CH2:26]2)(=[O:23])=[O:24])=[CH:35][CH:34]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 781262-PhenylethanethiolHCID 67051315HCID 67051315, compound

Product 1

HCID 67051248HCID 67051248, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

60% Sodium hydride (29 mg) was added to a solution of the product of step ii) (0.36 g) and 2-phenylethylthiol (0.1 g) in anhydrous DMF (4 ml) stirred under nitrogen. The reaction mixture was stirred for 18 h, diluted with EtOAc and washed with H2O. The separated organic solution was dried (MgSO4), filtered and the solvent evaporated under reduced pressure. The residue was purified by flash column chromatography on silica gel using Et2O/isohexane (3:7) as eluent to give the product as a white solid. Yield: 0.17 g.

Workup

  1. stirringThe reaction mixture was stirred for 18 h
  2. washwashed with H2O
  3. dry with materialThe separated organic solution was dried (MgSO4)
  4. filtrationfiltered
  5. customthe solvent evaporated under reduced pressure
  6. customThe residue was purified by flash column chromatography on silica gel

Sources & evidence

ORD record
ord-a714c7fd06bc433ba7ed5933bc6a026b
Source dataset
uspto-grants-2010_11
Patent number
US07838675B2

Reaction notes

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