m-Chloroperbenzoic acid → 3-Chlorobenzoic Acid

HRID 1971857Notes

Reaction equation

HRID 1971857 reaction equation
COC(C1N=C2N(CC(N3CC(C)CC(C)C3)=O)C=C(CSC)N2C(=O)C=1O)=O.[Cl:30][C:31]1[CH:32]=[C:33]([CH:38]=[CH:39][CH:40]=1)[C:34]([O:36]O)=[O:35]>ClCCl>[Cl:30][C:31]1[CH:32]=[C:33]([CH:38]=[CH:39][CH:40]=1)[C:34]([OH:36])=[O:35]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acid2×HCID 58126903HCID 58126903, compound

Product 1

HCID 4473-Chlorobenzoic AcidYield 269.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

1-[2-(3,5-dimethyl-piperidin-1-yl)-2-oxo-ethyl]-6-hydroxy-3-methylsulfanylmethyl-5-oxo-1,5-dihydro-imidazo[1,2-a]pyrimidine-7-carboxylic acid methyl ester from example 54 (0.35 g, 0.83 mmol) was dissolved in dichloromethane (10 ml) and cooled to 0° C. M-Chloroperoxybenzoic acid (0.286 g, 2 equivalents) were added. The reaction mixture was stirred for 2 hours, then more MCPBA (150 mg) was added, and the stirring was continued for one hour. The reaction was quenched with a solution of Na2S2O3, the aqueous phase was extracted with dichloromethane, dried over MgSO4 and evaporated to dryness to give the product as mixture with m-chlorobenzoic acid (0.7 g, treated as 100% yield, contains ˜50% m-Cl-benzoic acid by NMR).

Workup

  1. waitthe stirring was continued for one hour
  2. customThe reaction was quenched with a solution of Na2S2O3
  3. extractionthe aqueous phase was extracted with dichloromethane
  4. dry with materialdried over MgSO4
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-24618ebf21c5453b9b08a490622777cd
Source dataset
uspto-grants-2013_04
Patent number
US08431581B2

Reaction notes

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