Water → HCID 19086205, compound

HRID 1033101Notes

Reaction equation

HRID 1033101 reaction equation
[C:1]1([C:7]2[C:16]3[C:11](=[CH:12][C:13]([OH:17])=[CH:14][CH:15]=3)[CH:10]=[C:9]([CH2:18]Cl)[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[C:22]1([SH:28])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.O>CN(C=O)C>[C:1]1([C:7]2[C:16]3[C:11](=[CH:12][C:13]([OH:17])=[CH:14][CH:15]=3)[CH:10]=[C:9]([CH2:18][S:28][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7969ThiophenolHCID 24758Sodium hydrideHCID 10635636HCID 10635636, compound

Product 1

HCID 19086205HCID 19086205, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of the halide from Step 2 (600 mg, 0.22 mmoL) in dry DMF (5 mL) was added at r.t. NaH (90 mg, 2.2 mmoL), followed by thiophenol (114 mL, 1.1 mmoL). The reaction mixture was stirred at r.t. for 18 hr., then transferred to H2O and extracted with EtOAc. The combined organic phases were washed with brine, and dried over MgSO4. After evaporation of the solvent and purification by flash chromatography on silica gel (hexanes:EtOAc; 7:3) the title compound was obtained.

Workup

  1. extractionextracted with EtOAc
  2. washThe combined organic phases were washed with brine
  3. dry with materialdried over MgSO4
  4. customAfter evaporation of the solvent and purification by flash chromatography on silica gel (hexanes:EtOAc; 7:3) the title compound
  5. customwas obtained

Sources & evidence

ORD record
ord-4b9e21a989a34474a9074b20adca8737
Source dataset
uspto-grants-1994_05
Patent number
US05308852

Reaction notes

Loading…