m-Chloroperbenzoic acid → N-[2-[2-(1H-Tetrazol-5-yl)phenylsulfinyl]phenyl]-4-hexyloxybenzamide

HRID 1609296Notes

Reaction equation

HRID 1609296 reaction equation
[NH:1]1[C:5]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[S:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[NH:19][C:20](=[O:34])[C:21]2[CH:26]=[CH:25][C:24]([O:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])=[CH:23][CH:22]=2)=[N:4][N:3]=[N:2]1.ClC1C=CC=C(C(OO)=[O:43])C=1>C(Cl)(Cl)Cl>[NH:4]1[C:5]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[S:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[NH:19][C:20](=[O:34])[C:21]2[CH:22]=[CH:23][C:24]([O:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])=[CH:25][CH:26]=2)=[O:43])=[N:1][N:2]=[N:3]1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 178444961HCID 178444961, compound

Product 1

HCID 178444962N-[2-[2-(1H-Tetrazol-5-yl)phenylsulfinyl]phenyl]-4-hexyloxybenzamideYield 25.9%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 2.5 g of N-[2-[2-(1H-tetrazol-5yl)phenylthio]phenyl]-4-hexyloxybenzamide in 30 ml of chloroform was added 1.5 g of 80% m-chloroperbenzoic acid, and the mixture was stirred at room temperature for 2 hours, at the end of which time the solvent was distilled off. Then, ethyl acetate-chloroform was added to the residue and the resulting crystals were collected by filtration and recrystallized from ethanol-chloroform to give 0.67 g of the title compound as white crystals, m.p. 206°-210° C. (decomp.)

Workup

  1. distillationwas distilled off
  2. additionThen, ethyl acetate-chloroform was added to the residue
  3. filtrationthe resulting crystals were collected by filtration
  4. customrecrystallized from ethanol-chloroform

Sources & evidence

ORD record
ord-856363cd1f3147248f3727e92162f9bb
Source dataset
uspto-grants-1995_03
Patent number
US05399703

Reaction notes

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