m-Chloroperbenzoic acid → HCID 59136041, compound

HRID 1960486Notes

Reaction equation

HRID 1960486 reaction equation
[CH3:1][N:2]([C:12]1[CH:13]=[CH:14][CH:15]=[C:16]2[C:20]=1[NH:19][C:18]([C:21]1[S:22][CH:23]([CH2:26][N:27]3[CH2:32][CH2:31][S:30][CH2:29][CH2:28]3)[CH2:24][N:25]=1)=[CH:17]2)[S:3]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][N:7]=1)(=[O:5])=[O:4].ClC1C=CC=C(C(OO)=[O:41])C=1>ClCCl.C(OCC)(=O)C>[CH3:1][N:2]([C:12]1[CH:13]=[CH:14][CH:15]=[C:16]2[C:20]=1[NH:19][C:18]([C:21]1[S:22][CH:23]([CH2:26][N:27]3[CH2:32][CH2:31][S:30](=[O:41])[CH2:29][CH2:28]3)[CH2:24][N:25]=1)=[CH:17]2)[S:3]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][N:7]=1)(=[O:5])=[O:4]

Participants

5

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 57476296HCID 57476296, compound

Product 1

HCID 59136041HCID 59136041, compoundYield 21%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of N-methyl-N-{2-[5-(thiomorpholinomethyl)-4,5-dihydro-1,3-thiazol-2-yl]-1H-indol-7-yl}pyridine-2-sulfonamide (180 mg) in dichloromethane(8 mL) was added m-chloroperbenzoic acid (75 mL) under ice-cooling, and the mixture was stirred for 3 hr under ice-cooling. The reaction solution was diluted with ethyl acetate, washed with aqueous sodium hydrogencarbonate solution and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to basic silica gel column chromatography (ethyl acetate:hexane=6:4-9:1), and the obtained colorless oil was crystallized from ethyl acetate-hexane to give the title compound (39 mg, yield: 21%) as colorless needle crystals. MS:504(MH+). melting point 193-194° C.

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. washwashed with aqueous sodium hydrogencarbonate solution and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customthe obtained colorless oil was crystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-9db86dda35d349f28fd4dc7ca6035627
Source dataset
uspto-grants-2013_04
Patent number
US08410087B2

Reaction notes

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