Sodium hydride → HCID 68431311, compound

HRID 2244022Notes

Reaction equation

HRID 2244022 reaction equation
[OH:1][C:2]1[C:7]([CH2:8][CH2:9][CH3:10])=[C:6]([OH:11])[CH:5]=[CH:4][C:3]=1[C:12](=[O:14])[CH3:13].[H-].[Na+].Br[CH2:18][C:19]1[CH:24]=[CH:23][C:22]([S:25]([NH:28][C:29]2[CH:34]=[CH:33][CH:32]=[C:31]([C:35]#[N:36])[CH:30]=2)(=[O:27])=[O:26])=[CH:21][CH:20]=1>CN(C)C=O.[Cl-].[Na+].O>[C:12]([C:3]1[CH:4]=[CH:5][C:6]([O:11][CH2:18][C:19]2[CH:24]=[CH:23][C:22]([S:25]([NH:28][C:29]3[CH:34]=[CH:33][CH:32]=[C:31]([C:35]#[N:36])[CH:30]=3)(=[O:27])=[O:26])=[CH:21][CH:20]=2)=[C:7]([CH2:8][CH2:9][CH3:10])[C:2]=1[OH:1])(=[O:14])[CH3:13]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 27751982',4'-Dihydroxy-3'-propylacetophenoneHCID 65480008HCID 65480008, compound

Product 1

HCID 68431311HCID 68431311, compoundYield 35.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 57417360Sodium chloride; waterSolvent

Procedure

Add 1-(2,4-dihydroxy-3-propyl-phenyl)-ethanone (2.77 g, 14.2 mmol) to sodium hydride (396 mg, 15.7 mmol) in dimethylformamide (20 mL) at 0° C., stir 10 minutes, add 4-bromomethyl-N-(3-cyano-phenyl)-benzenesulfonamide (2.50 g, 7.12 mmol) in dimethylformamide (15 mL) drop wise via addition funnel. After 2 hours at ambient temperature, pour into brine (40 mL), extract with ethyl acetate (2×40 mL), dry organic phase over sodium sulfate, filter and concentrate under reduced pressure. Purify residue by flash chromatography to yield the title compound (1.17 g, 2.52 mmol): MS (m/z): 463 (M−1).

Workup

  1. additionwise via addition funnel
  2. waitAfter 2 hours at ambient temperature
  3. extractionextract with ethyl acetate (2×40 mL), dry organic phase over sodium sulfate
  4. filtrationfilter
  5. concentrationconcentrate under reduced pressure

Sources & evidence

ORD record
ord-1694dda192794e309f83b5ac3c30b8ca
Source dataset
uspto-grants-2010_03
Patent number
US07678794B2

Reaction notes

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