m-Chloroperbenzoic acid → N-cyclopropyl-1-{4-[(ethylamino)carbonyl]phenyl}-5-[(phenylsulfonyl)methyl]-1H-1,2,3-triazole-4-carboxamide

HRID 1717360Notes

Reaction equation

HRID 1717360 reaction equation
[CH:1]1([NH:4][C:5]([C:7]2[N:8]=[N:9][N:10]([C:21]3[CH:26]=[CH:25][C:24]([C:27]([NH:29][CH2:30][CH3:31])=[O:28])=[CH:23][CH:22]=3)[C:11]=2[CH2:12][S:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[O:14])=[O:6])[CH2:3][CH2:2]1.ClC1C=CC=C(C(OO)=[O:40])C=1>C1COCC1.C(OCC)(=O)C>[CH:1]1([NH:4][C:5]([C:7]2[N:8]=[N:9][N:10]([C:21]3[CH:22]=[CH:23][C:24]([C:27]([NH:29][CH2:30][CH3:31])=[O:28])=[CH:25][CH:26]=3)[C:11]=2[CH2:12][S:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)(=[O:40])=[O:14])=[O:6])[CH2:2][CH2:3]1

Participants

5

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 57665018N-cyclopropyl-1-{4-[(ethylamino)carbonyl]phenyl}-5-[(phenylsulfinyl)methyl]-1H-1,2,3-triazole-4-carboxamide

Product 1

HCID 57665196N-cyclopropyl-1-{4-[(ethylamino)carbonyl]phenyl}-5-[(phenylsulfonyl)methyl]-1H-1,2,3-triazole-4-carboxamideYield 100%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

N-Cyclopropyl-1-{4-[(ethylamino)carbonyl]phenyl}-5-[(phenylsulfinyl)methyl]-1H-1,2,3-triazole-4-carboxamide (107 mg, 0.24 mmol) obtained in Example 313 was dissolved in THF (2.0 ml), m-chloroperbenzoic acid (purity 65%, 64 mg, 0.24 mmol, 1.0 eq.) was added with stirring at 0° C., and the mixture was stirred for 1 hr and at room temperature for 2 hr. The reaction mixture was diluted with ethyl acetate (25 ml), washed with 5% aqueous sodium sulfite solution, 2% aqueous sodium carbonate solution and saturated brine, dried over anhydrous sodium sulfate and concentrated. Diethyl ether was added to the residue, and the precipitate was collected by filtration, washed with diethyl ether and dried to give the title compound as a white powder (111 mg, 0.24 mmol, quant.).

Workup

  1. stirringthe mixture was stirred for 1 hr and at room temperature for 2 hr
  2. washwashed with 5% aqueous sodium sulfite solution, 2% aqueous sodium carbonate solution and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. additionDiethyl ether was added to the residue
  6. filtrationthe precipitate was collected by filtration
  7. washwashed with diethyl ether
  8. customdried

Sources & evidence

ORD record
ord-4154b80be0b74385b909d824eff18b59
Source dataset
uspto-grants-2010_09
Patent number
US07803822B2

Reaction notes

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