Acetyl chloride → HCID 86744602, compound

HRID 981466Notes

Reaction equation

HRID 981466 reaction equation
[OH:1][CH:2]([CH:6]([S:21][CH2:22][C:23](=[O:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=1)[C:3]([NH2:5])=[O:4].[C:31](Cl)(=[O:33])[CH3:32]>C(Cl)Cl.N1C=CC=CC=1.O>[C:31]([O:1][CH:2]([CH:6]([S:21][CH2:22][C:23](=[O:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=1)[C:3]([NH2:5])=[O:4])(=[O:33])[CH3:32]

Participants

6

Reactant 2

HCID 6367Acetyl chlorideHCID 86744603alpha-Hydroxy-4-methoxyphenyl-beta-[(2-oxo-2-phenylethyl) thio]benzenepropanamide

Product 1

HCID 86744602HCID 86744602, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1049PyridineSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 3.5 g (0.01 mol) of rac.-(R,*S*)α-(hydroxy)-4-methoxyphenyl-β-[(2-oxo -2-phenYlethYl)thio]benzenepropanamide in 130 mL of methylene chloride and 4.4 mL of pyridine was added dropwise at ice-bath temperature a solution of 1.1 g (0.014 mol) of acetyl chloride in 25 mL of methylene chloride. The mixture was stirred at this temperature for one hour then at room temperature for 17 hrs and diluted with water. The aqueous suspension was extracted with methylene chloride and the combined organic solutions were washed with water and dried (MgSO4). Removal of the solvent gave the crude ester, which after crystallization from ethyl acetate afforded 2.9 g (74%) of rac.-(S,*R*)-α-(acetyloxy)-4-methoxyphenyl -β-[(2-oxo-2-phenylethyl) thio]benzenepropanamide, mp 122°-123°.

Workup

  1. waitat room temperature for 17 hrs
  2. extractionThe aqueous suspension was extracted with methylene chloride
  3. washthe combined organic solutions were washed with water
  4. dry with materialdried (MgSO4)
  5. customRemoval of the solvent
  6. customgave the crude ester, which
  7. customafter crystallization from ethyl acetate

Sources & evidence

ORD record
ord-901a9a0e64814da7a78659358ed1cc22
Source dataset
uspto-grants-1991_02
Patent number
US04992432

Reaction notes

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