2-mercapto-1-phenylethanone → HCID 86744603, compound

HRID 981464

Reaction equation

HRID 981464 reaction equation
[SH:1][CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:4].CO[C:13]1[CH:18]=[CH:17][C:16]([CH:19]2[O:21][CH:20]2[C:22]([NH2:24])=[O:23])=[CH:15][CH:14]=1.C(Cl)Cl.[C:28]([O:31][CH2:32][CH3:33])(=O)C>C1(C)C=CC=CC=1>[OH:21][CH:20]([CH:19]([S:1][CH2:2][C:3](=[O:4])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[C:16]1[CH:15]=[CH:14][CH:13]=[CH:18][C:17]=1[C:3]1[CH:2]=[CH:33][C:32]([O:31][CH3:28])=[CH:6][CH:5]=1)[C:22]([NH2:24])=[O:23]

Participants

5

Reactant 3

HCID 110736092-mercapto-1-phenylethanoneHCID 148559763-(4-Methoxyphenyl)oxiranecarboxamideHCID 21226138Dichloromethane ethylacetate

Product 1

HCID 86744603HCID 86744603, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 8.1 g (0.053 mol) of 2-mercapto-1-phenylethanone in 100 mL of toluene under nitrogen was added 10.2 g (0.053 mol) of 3-(4-methoxyphenyl)oxiranecarboxamide and the mixture was stirred and heated in an oil bath at 120o for 3 hrs. The solvent was removed under reduced pressure to give 18.1 g of crude product, which was dissolved in a minimum amount of a mixture of methylene chloride--ethyl acetate (8:2) and chromatographed using a Waters Prep. LC-system 500 A. Eluted with the same solvents and 200 mL fractions were collected. Fractions 18-21 provided 9.3 g of crude product of which was rechromatographed using ethyl acetate--hexane (75:25) as elutants. Fraction 7 after removal of the solvent yielded a residue, which after crystallization from ethyl acetate gave 0.9 g (5%) of rac.-(R,*R*)-α-hydroxy-4-methoxyphenyl-β-[ (2-oxo-2-phenylethyl)thio]benzenepropanamide, mp 132°-134°.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customto give 18.1 g of crude product, which
  3. customchromatographed
  4. washEluted with the same solvents and 200 mL fractions
  5. customwere collected
  6. customFractions 18-21 provided 9.3 g of crude product of which
  7. customwas rechromatographed
  8. customFraction 7 after removal of the solvent
  9. customyielded a residue, which
  10. customafter crystallization from ethyl acetate

Sources & evidence

ORD record
ord-185f979573e142fdb219ef971acf37b2
Source dataset
uspto-grants-1991_02
Patent number
US04992432

Linked notes

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