Dichloromethane → HCID 57668008, compound

HRID 2191629Notes

Reaction equation

HRID 2191629 reaction equation
ClCCl.Cl.[CH3:5][C:6]1[CH:12]=[CH:11][C:10]([O:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:9][C:7]=1[NH2:8].[C:20](OC(=O)C)(=[O:22])[CH3:21]>N1C=CC=CC=1>[CH3:5][C:6]1[CH:12]=[CH:11][C:10]([O:13][C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)=[CH:9][C:7]=1[NH:8][C:20](=[O:22])[CH3:21]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 7918Acetic AnhydrideHCID 67344504HCID 67344504, compound

Product 1

HCID 57668008HCID 57668008, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To dichloromethane 5.0 mL solution of 2-methyl-5-phenoxyaniline hydrochloride 0.50 g were added pyridine 0.34 mL and acetic anhydride 0.24 mL under ice cooling, and it was stirred at room temperature for 6 hours and 30 minutes. The solvent was removed under reduced pressure,1.0 mol/L hydrochloric acid and ethyl acetate were added to the obtained residue. The organic layer was separated and collected,dried over anhydrous magnesium sulfate after sequential washing with saturated sodium hydrogen carbonate aqueous solution 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-(2-methyl-5-phenoxyphenyl)acetamide 0.44 g of white solid.

Workup

  1. customThe solvent was removed under reduced pressure,1.0 mol/L hydrochloric acid and ethyl acetate
  2. additionwere added to the obtained residue
  3. customThe organic layer was separated
  4. washafter sequential washing with saturated sodium hydrogen carbonate aqueous solution and saturated sodium chloride aqueous solution
  5. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-df8c586996334f85ac4501e6fb63e7a4
Source dataset
uspto-grants-2012_12
Patent number
US08327467B2

Reaction notes

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