m-Chloroperbenzoic acid → HCID 9817402, compound

HRID 1003413Notes

Reaction equation

HRID 1003413 reaction equation
[C:1]([C:3]1[C:4](=[O:19])[NH:5][C:6]([C:9]2[CH:14]=[CH:13][C:12]([S:15][CH3:16])=[CH:11][C:10]=2[O:17][CH3:18])=[CH:7][CH:8]=1)#[N:2].ClC1C=CC=C(C(OO)=[O:28])C=1>ClCCl>[C:1]([C:3]1[C:4](=[O:19])[NH:5][C:6]([C:9]2[CH:14]=[CH:13][C:12]([S:15]([CH3:16])=[O:28])=[CH:11][C:10]=2[O:17][CH3:18])=[CH:7][CH:8]=1)#[N:2]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 9881949HCID 9881949, compound

Product 1

HCID 9817402HCID 9817402, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3-cyano-6-(2-methoxy-4-methylthiophenyl)-2(1H)-pyridinone (1.24 g) in dichloromethane (500 ml) was treated with m-chloroperbenzoic acid (85%, 0.92 g). After 2 hours the solution was washed with sodium bicarbonate solution and evaporated to give the crude product (1.27 g, m.p. 239-241° C.). Purification by chromatography (silica, dichloromethane) followed by recrystallization from aqueous ethanol yielded the pure title compound, 0.81 g, m.p. 243-245° C.

Workup

  1. washAfter 2 hours the solution was washed with sodium bicarbonate solution
  2. customevaporated
  3. customto give the crude product (1.27 g, m.p. 239-241° C.)
  4. customPurification by chromatography (silica, dichloromethane)
  5. customfollowed by recrystallization from aqueous ethanol

Sources & evidence

ORD record
ord-88d4de479b0348938e7097021fcd1c23
Source dataset
uspto-grants-2000_04
Patent number
US06046216

Reaction notes

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