m-Chloroperbenzoic acid → HCID 118666349, compound

HRID 630467Notes

Reaction equation

HRID 630467 reaction equation
ClC1C=C(C=CC=1)C(OO)=[O:6].[F:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[C:19]1[CH:20]=[N:21][C:22]([N:25]2[C:33]3[C:28](=[CH:29][CH:30]=[C:31]([C:34]([O:36][CH3:37])=[O:35])[CH:32]=3)[C:27]([S:38][CH3:39])=[CH:26]2)=[N:23][CH:24]=1>ClCCl>[F:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[C:19]1[CH:20]=[N:21][C:22]([N:25]2[C:33]3[C:28](=[CH:29][CH:30]=[C:31]([C:34]([O:36][CH3:37])=[O:35])[CH:32]=3)[C:27]([S:38]([CH3:39])=[O:6])=[CH:26]2)=[N:23][CH:24]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 131735393HCID 131735393, compound

Product 1

HCID 118666349HCID 118666349, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

m-Chloroperoxybenzoic acid (77%, 0.98 g, 4.38 mmol) in dichloromethane (5 mL) was added dropwise to an ice-cooled solution of 51c) (2.3 g, 5.85 mmol) in dichloromethane (25 mL). The resulting mixture was stirred at room temperature for 2 h, then diluted with dichloromethane (50 mL), and successively washed with saturated sodium hydrogen carbonate solution (2×50 mL) and brine (1×50 mL). The organic phase was dried over sodium sulfate and evaporated to obtain the crude product that was purified by column chromatography [100-200 mesh silica; 2% methanol in dichloromethane]. White solid. Yield: 2.2 g (92% of theory). HPLC-MS (method 5): Rt=3.38 min; m/z [M+H]+=410

Workup

  1. washsuccessively washed with saturated sodium hydrogen carbonate solution (2×50 mL) and brine (1×50 mL)
  2. dry with materialThe organic phase was dried over sodium sulfate
  3. customevaporated

Sources & evidence

ORD record
ord-4e52c37be492416386ff8a8b9ada46a5
Source dataset
uspto-grants-2016_04
Patent number
US09315490B2

Reaction notes

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