Sodium hydride → HCID 19689348, compound

HRID 2101Notes

Reaction equation

HRID 2101 reaction equation
Br[CH2:2][CH2:3][CH2:4][S:5]([CH2:8][C:9]1[CH:23]=[CH:22][C:12]([C:13]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=2)=[O:14])=[CH:11][CH:10]=1)(=[O:7])=[O:6].[H-].[Na+].CN(C)C(=O)C>O>[Cl:21][C:18]1[CH:19]=[CH:20][C:15]([C:13]([C:12]2[CH:22]=[CH:23][C:9]([CH:8]3[CH2:2][CH2:3][CH2:4][S:5]3(=[O:7])=[O:6])=[CH:10][CH:11]=2)=[O:14])=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 31374DimethylacetamideHCID 19689375HCID 19689375, compound

Product 1

HCID 19689348HCID 19689348, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4-(3-bromopropyl)sulfonylmethyl-4'-chlorobenzophenone (2.5 g) and 60% sodium hydride (0.3 g) were added to N,N-dimethylacetamide (70 ml), and the mixture was stirred for 16 hours at room temperature. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with water and then dried over anhydrous magnesium sulfate. Ethyl acetate was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=1:1) to obtain the desired product as a slightly yellow viscous substance 1.0 g, yield: 50%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationEthyl acetate was distilled off under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-8621c7ae01154702b393326bf088b608
Source dataset
uspto-grants-1998_03
Patent number
US05728699

Reaction notes

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