m-Chloroperbenzoic acid → HCID 44631629, compound

HRID 901079Notes

Reaction equation

HRID 901079 reaction equation
[CH3:1][S:2][C:3]1[CH:8]=[CH:7][C:6]([C@H:9]2[O:13][C:12]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[N:11][C@@H:10]2[CH2:20][OH:21])=[CH:5][CH:4]=1.ClC1C=CC=C(C(OO)=[O:30])C=1>ClCCl>[CH3:1][S:2]([C:3]1[CH:4]=[CH:5][C:6]([C@H:9]2[O:13][C:12]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[N:11][C@@H:10]2[CH2:20][OH:21])=[CH:7][CH:8]=1)=[O:30]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 11022935HCID 11022935, compound

Product 1

HCID 44631629HCID 44631629, compoundYield 99.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-78 °C

Procedure

To a solution of sulfide 18 (5 g, 16.7 mmol) in dichloromethane (200 mL) at −78° C. was added m-chloroperbenzoic acid (3.6 g, 16.7 mmol) in dichloromethane (150 mL) over a span of 10 minutes. The resulting mixture was stirred at −78° C. for 30 minutes. The reaction was quenched with aqueous NaHCO3 at −78° C. Extraction with dichloromethane (3×200 mL) afforded 5.22 g of the desired sulfoxide as a white solid, upon concentration. 1H NMR (200 MHz, CDCl3) 2.72 (s, 3H), 3.80-3.90 (m, 1H), 4.05-4.15 (m, 1H), 4.20-4.30 (m, 1H), 5.61 (d, J=8 Hz, 1H), 7.35-7.55 (m, 5H), 7.68 (t, J=9 Hz, 2H), 8.0 (d, J=9 Hz, 2H).

Workup

  1. customThe reaction was quenched with aqueous NaHCO3 at −78° C
  2. extractionExtraction with dichloromethane (3×200 mL)

Sources & evidence

ORD record
ord-72c70015d49d4309ae66c9664a0cafae
Source dataset
uspto-grants-2008_04
Patent number
US07361689B2

Reaction notes

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