Acetanilide → HCID 86617323, compound

HRID 661736Notes

Reaction equation

HRID 661736 reaction equation
CN(C=O)C.[C:6]([NH:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)(=[O:8])[CH3:7].[H-].[Na+].[C:18]1([N:24]=[C:25]([O:37][C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[CH:26]=[CH:27]S(C2C=CC=CC=2)(=O)=O)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C(OCC)(=O)C>[C:18]1([N:24]=[C:25]([O:37][C:38]2[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=2)[CH:26]=[CH:27][N:9]([C:6](=[O:8])[CH3:7])[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

6

Reactant 4

HCID 904AcetanilideHCID 6228Dimethylformamide2×HCID 24758Sodium hydrideHCID 86617322HCID 86617322, compound

Product 1

HCID 86617323HCID 86617323, compoundYield 17%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To DMF (3 ml) solution of acetanilide (0.14 g) was added sodium hydride (60% in oil: 0.043 g) under ice-cooling, and DMF (2 ml) solution of phenyl N-phenyl-3-(phenylsulfonyl)acrylimidate (0.30 g) was added dropwise. It was stirred for two hours under ice-cooling and for one hour at room temperature. Ethyl acetate (100 ml) was added to the reaction mixture and was successively washed with water and aqueous saturated sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate, concentrated under reduced pressure. The residue was isolated and purified by silica gel column chromatography (hexane:ethyl acetate=3:1) to obtain phenyl N-phenyl-3-(N′-acetyl-N′-phenylamino)acrylimidate (0.050 g) as yellow crystal.

Workup

  1. temperaturecooling
  2. washwas successively washed with water and aqueous saturated sodium chloride solution
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was isolated
  6. custompurified by silica gel column chromatography (hexane:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-38201591c50c4fb390c25ae8d250669d
Source dataset
uspto-grants-2011_12
Patent number
US08084644B2

Reaction notes

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