m-Chloroperbenzoic acid → HCID 19354588, compound

HRID 377554Notes

Reaction equation

HRID 377554 reaction equation
ClC1C=C(C=CC=1)C(OO)=[O:6].[F:12][C:13]1[CH:18]=[CH:17][C:16]([F:19])=[CH:15][C:14]=1[NH:20][C:21](=[O:41])[C:22]([N:25]1[C:30](=[O:31])[C:29]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[C:28]([CH2:38][S:39][CH3:40])[O:27][CH2:26]1)([CH3:24])[CH3:23]>ClCCl>[F:12][C:13]1[CH:18]=[CH:17][C:16]([F:19])=[CH:15][C:14]=1[NH:20][C:21](=[O:41])[C:22]([N:25]1[C:30](=[O:31])[C:29]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[C:28]([CH2:38][S:39]([CH3:40])=[O:6])[O:27][CH2:26]1)([CH3:24])[CH3:23]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 11812072HCID 11812072, compound2×

Product 1

HCID 19354588HCID 19354588, compoundYield 36.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-20 °C

Procedure

m-Chloroperoxybenzoic acid (75% pure, 0.54 g) was added to a stirred solution of N-(2,5-difluorophenyl)-2-(2,3-dihydro-6-methylthiomethyl-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methylpropanamide (compound 1, 100 g) in dichloromethane at -20° C. The mixture was stirred at -20° C. for 1 hour, diluted with dichloromethane, washed with 1M sodium carbonate, dried (magnesium sulphate) and solvent evaporated under reduced pressure. The residue was triturated with diethyl ether to give N-(2,5-difluorophenyl)-2-(2,3-dihydro-6-methylsulphinylmethyl-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methylpropanamide (compound 5, 0.51 g) as a white solid, m.p. 124-128° C.

Workup

  1. washwashed with 1M sodium carbonate
  2. dry with materialdried (magnesium sulphate) and solvent
  3. customevaporated under reduced pressure
  4. customThe residue was triturated with diethyl ether

Sources & evidence

ORD record
ord-65881a3197da4391bebafddaee13e991
Source dataset
uspto-grants-2000_02
Patent number
US06028032

Reaction notes

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