Sodium hydride → HCID 23039700, compound

HRID 1770360Notes

Reaction equation

HRID 1770360 reaction equation
[H-].[Na+].[I-].[CH3:4][S+](C)C.[Cl:8][C:9]1[CH:14]=[C:13]([O:15][C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=2)[CH:12]=[CH:11][C:10]=1[C:23](=[O:25])[CH3:24].[NH4+].[Cl-]>C1COCC1.CS(C)=O>[Cl:8][C:9]1[CH:14]=[C:13]([O:15][C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=2)[CH:12]=[CH:11][C:10]=1[C:23]1([CH3:4])[CH2:24][O:25]1

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 75127Trimethylsulfonium iodideHCID 6774791-[2-Chloro-4-(4-chlorophenoxy)phenyl]ethan-1-one

Product 1

HCID 23039700HCID 23039700, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent3×HCID 8028TetrahydrofuranSolvent

Procedure

DMSO (150 mL) was added dropwise to a mixture of sodium hydride (22 g) in THF (600 mL). After completion of the addition a solution of trimethylsulfonium iodide (171 g) in DMSO (300 mL) was added slowly at 5° C. whereupon a solution of 1-[2-chloro-4-(4-chlorophenoxy)phenyl]ethanone (107 g) in DMSO (300 mL) was added carefully. The mixture was stirred for 1 h at room temperature and dil. NH4Cl solution was added. The mixture was extracted with MTBE (3×) and the combined organic phases were washed with water, dried and evaporated to obtain the desired compound that was used without further purification.

Workup

  1. additionwas added carefully
  2. extractionThe mixture was extracted with MTBE (3×)
  3. washthe combined organic phases were washed with water
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-b37ba3fbf1c34340a361306fe0dd4206
Source dataset
uspto-grants-2016_02
Patent number
US09247746B2

Reaction notes

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