Hydrochloric Acid → HCID 57668003, compound

HRID 2191626Notes

Reaction equation

HRID 2191626 reaction equation
[H-].[Na+].[C:3](Cl)(=[O:5])[CH3:4].[F:7][C:8]1[CH:29]=[CH:28][C:11]([NH:12][C:13]2[CH:14]=[C:15]([CH:24]=[CH:25][C:26]=2[CH3:27])[C:16]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:17])=[CH:10][CH:9]=1.Cl>C(OCC)(=O)C.CN(C)C=O>[C:16]([C:15]1[CH:24]=[CH:25][C:26]([CH3:27])=[C:13]([N:12]([C:11]2[CH:10]=[CH:9][C:8]([F:7])=[CH:29][CH:28]=2)[C:3](=[O:5])[CH3:4])[CH:14]=1)(=[O:17])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6367Acetyl chloride2×HCID 24758Sodium hydride2×HCID 57667979HCID 57667979, compound

Product 1

HCID 57668003HCID 57668003, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

60% sodium hydride 79 mg and acetyl chloride 0.14 mL were added to N,N-dimethylformamide 5.0 mL solution of 3-(4-fluoroanilino)-4-methylbenzophenone 0.50 g under ice cooling sequentially, and it was stirred at room temperature for 4 hours. After the reaction mixture was cooled to ice temperature,60% sodium hydride 79 mg and acetyl chloride 0.14 mL were added sequentially, and it was stirred at room temperature for 5 hours and 30 minutes. Ethyl acetate and 1.0 mol/L hydrochloric acid were added to the reaction mixture. The organic layer was separated and collected,dried over anhydrous magnesium sulfate after sequential washing with 1.0 mol/L hydrochloric acid and saturated sodium chloride aqueous solution, and the solvent was removed under reduced pressure. The obtained residue was refined by silica gel column chromatography [Fuji SILYSIA Chemical Ltd., PSQ100B(spherical type), eluent; hexane:ethyl acetate=2:1] to give N-(5-benzoyl-2-methylphenyl)-N-(4-fluorophenyl)acetamide 82 mg of orange oil.

Workup

  1. additionwere added sequentially
  2. stirringit was stirred at room temperature for 5 hours and 30 minutes
  3. customThe organic layer was separated
  4. washafter sequential washing with 1.0 mol/L hydrochloric acid and saturated sodium chloride aqueous solution
  5. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-5f16f6f7a7844b40ad63a838d2f6c4ab
Source dataset
uspto-grants-2012_12
Patent number
US08327467B2

Reaction notes

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