m-Chloroperbenzoic acid → 2-(4-Chloro-phenylsulfonylamino)-4,5-dimethoxy-N-(4-(1-oxo-thiomorpholine-4-sulfonyl)-phenyl)-benzamide

HRID 2053375Notes

Reaction equation

HRID 2053375 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2[CH:35]=[C:34]([O:36][CH3:37])[C:33]([O:38][CH3:39])=[CH:32][C:13]=2[C:14]([NH:16][C:17]2[CH:22]=[CH:21][C:20]([S:23]([N:26]3[CH2:31][CH2:30][S:29][CH2:28][CH2:27]3)(=[O:25])=[O:24])=[CH:19][CH:18]=2)=[O:15])(=[O:10])=[O:9])=[CH:4][CH:3]=1.ClC1C=CC=C(C(OO)=[O:48])C=1>CC(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2[CH:35]=[C:34]([O:36][CH3:37])[C:33]([O:38][CH3:39])=[CH:32][C:13]=2[C:14]([NH:16][C:17]2[CH:18]=[CH:19][C:20]([S:23]([N:26]3[CH2:27][CH2:28][S:29](=[O:48])[CH2:30][CH2:31]3)(=[O:25])=[O:24])=[CH:21][CH:22]=2)=[O:15])(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 99605422-[[(4-Chlorophenyl)sulfonyl]amino]-4,5-dimethoxy-N-[4-(4-thiomorpholinylsulfonyl)phenyl]benzamide

Product 1

HCID 224958462-(4-Chloro-phenylsulfonylamino)-4,5-dimethoxy-N-(4-(1-oxo-thiomorpholine-4-sulfonyl)-phenyl)-benzamide

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

500 mg (0.82 mmol) of 2-(4-chloro-phenylsulfonylamino)-4,5-dimethoxy-N-(4-(thiomorpholine-4-sulfonyl)-phenyl)-benzamide in 50 ml of acetone were cooled to 0° C. A solution of 371 mg (1.23 mmol) of 57% m-chloroperbenzoic acid in 20 ml of acetone was added and the mixture was stirred at room temperature over night. For working up it was poured onto water/ice and the precipitate was filtered off with suction. The two products obtained as a mixture were separated by chromatography over silica with methylene chloride/methanol (97:3).

Workup

  1. additionwas poured onto water/ice
  2. filtrationthe precipitate was filtered off with suction
  3. customThe two products obtained as a mixture
  4. customwere separated by chromatography over silica with methylene chloride/methanol (97:3)

Sources & evidence

ORD record
ord-ddf370a3cdf84703a0617dc08608df1c
Source dataset
uspto-grants-2008_02
Patent number
US07326789B2

Reaction notes

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