m-Chloroperbenzoic acid → HCID 58266520, compound

HRID 1505912Notes

Reaction equation

HRID 1505912 reaction equation
[Br:1][C:2]1[CH:14]=[CH:13][C:5]([CH2:6][N:7]2[CH2:12][CH2:11][S:10][CH2:9][CH2:8]2)=[CH:4][CH:3]=1.ClC1C=CC=C(C(OO)=[O:23])C=1>C(Cl)Cl>[Br:1][C:2]1[CH:14]=[CH:13][C:5]([CH2:6][N:7]2[CH2:8][CH2:9][S:10](=[O:23])[CH2:11][CH2:12]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 785841HCID 785841, compound

Product 1

HCID 58266520HCID 58266520, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-(4-bromobenzyl)-thiomorpholine (0.20 g, 0.735 mmol) was dissolved in DCM (10 mL) under a nitrogen atmosphere and m-chloroperbenzoic acid (0.13 g, 0.74 mmol) was added portionwise. The reaction mixture was stirred at room temperature for 1 h then purified by flash chromatography (silica, Biotage 50 g column, 0-75% (10% methanol in DCM)) to afford the title compound (0.125 g, 59%). 1H NMR (DMSO-D6, 400 MHz): 7.55-7.49 (m, 2H), 7.31-7.25 (m, 2H), 3.53 (s, 2H), 2.92-2.80 (m, 4H), 2.78-2.65 (m, 2H), 2.64-2.54 (m, 2H). LCMS (Method G): RT=2.66 min, M+H+=289.

Workup

  1. customthen purified by flash chromatography (silica, Biotage 50 g column, 0-75% (10% methanol in DCM))

Sources & evidence

ORD record
ord-5b14364da02247af95cc93625fd4d0c9
Source dataset
uspto-grants-2015_12
Patent number
US09216980B2

Reaction notes

Loading…