m-Chloroperbenzoic acid → HCID 86599517, compound

HRID 2221361Notes

Reaction equation

HRID 2221361 reaction equation
C(=O)([O-])[OH:2].[Na+].[Cl:6][C:7]1[CH:29]=[CH:28][C:10]([CH2:11][NH:12][C:13](=[O:27])[CH2:14][C:15]2[CH:16]=[C:17]3[C:22](=[CH:23][CH:24]=2)[O:21][C:20]([CH3:26])([CH3:25])[CH:19]=[CH:18]3)=[CH:9][CH:8]=1.C1C=C(Cl)C=C(C(OO)=O)C=1>ClCCl>[Cl:6][C:7]1[CH:8]=[CH:9][C:10]([CH2:11][NH:12][C:13](=[O:27])[CH2:14][C:15]2[CH:24]=[CH:23][C:22]3[O:21][C:20]([CH3:26])([CH3:25])[CH:19]4[O:2][CH:18]4[C:17]=3[CH:16]=2)=[CH:28][CH:29]=1

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 69057418HCID 69057418, compound

Product 1

HCID 86599517HCID 86599517, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

700 ml of a saturated aqueous sodium hydrogen carbonate solution was added to a solution of 21.92 g of the N-4-chlorobenzyl-2-(2,2-dimethyl-2H-chromen-6-yl) acetamide obtained above in 600 ml dichloromethane. A total of 31.6 g MCPBA (72%) was added in portions to this receiving solution and stirred for 16 hours at room temperature. The organic phase was separated, washed twice with a 5%-strength aqueous sodium hydrogen carbonate solution, dried over sodium sulfate and substantially completely evaporated at reduced pressure. Drying in an oil pump vacuum yielded N-(4-chlorobenzyl)-2-(2,2-dimethyl-1a,7b-dihydro-2H-oxireno[c]chromen-6-yl)acetamide as crude oil, which was used without further purification or characterization for the subsequent reaction.

Workup

  1. customThe organic phase was separated
  2. washwashed twice with a 5%-strength aqueous sodium hydrogen carbonate solution
  3. dry with materialdried over sodium sulfate
  4. customsubstantially completely evaporated at reduced pressure
  5. customDrying in an oil pump vacuum

Sources & evidence

ORD record
ord-8615d62891494996bbf1ccdfea77a9f7
Source dataset
uspto-grants-2008_05
Patent number
US07368582B2

Reaction notes

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