m-Chloroperbenzoic acid → 1-[2-(2-Methyl-4-{2-[2-(E)-(4-trifluoromethoxy-phenyl)-vinyl]-oxazol-4-ylmethoxy}-phenylmethanesulfonyl)-ethyl]-1H-[1,2,3]triazole

HRID 892261Notes

Reaction equation

HRID 892261 reaction equation
ClC1C=C(C=CC=1)C(OO)=[O:6].[CH3:12][C:13]1[CH:18]=[C:17]([O:19][CH2:20][C:21]2[N:22]=[C:23](/[CH:26]=[CH:27]/[C:28]3[CH:33]=[CH:32][C:31]([O:34][C:35]([F:38])([F:37])[F:36])=[CH:30][CH:29]=3)[O:24][CH:25]=2)[CH:16]=[CH:15][C:14]=1[CH2:39][S:40]([CH2:42][CH2:43][N:44]1[CH:48]=[CH:47][N:46]=[N:45]1)=[O:41]>C(OCC)(=O)C.ClCCl>[CH3:12][C:13]1[CH:18]=[C:17]([O:19][CH2:20][C:21]2[N:22]=[C:23](/[CH:26]=[CH:27]/[C:28]3[CH:29]=[CH:30][C:31]([O:34][C:35]([F:37])([F:36])[F:38])=[CH:32][CH:33]=3)[O:24][CH:25]=2)[CH:16]=[CH:15][C:14]=1[CH2:39][S:40]([CH2:42][CH2:43][N:44]1[CH:48]=[CH:47][N:46]=[N:45]1)(=[O:6])=[O:41]

Participants

5

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 222420681-[2-(2-Methyl-4-{2-[2-(e)-(4-trifluoromethoxy-phenyl)-vinyl]-oxazol-4-ylmethoxy}-phenyl-methanesulfinyl)-ethyl]-1h[1,2,3]triazole

Product 1

HCID 115412331-[2-(2-Methyl-4-{2-[2-(E)-(4-trifluoromethoxy-phenyl)-vinyl]-oxazol-4-ylmethoxy}-phenylmethanesulfonyl)-ethyl]-1H-[1,2,3]triazoleYield 53%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

35 mg (0.15 mmol) 75% 3-chloroperoxybenzoic acid dissolved in 5 ml ethyl acetate were given at −30° C. to solution of 52 mg (0.10 mmol) 1-[2-(2-methyl-4-{2-[2-(E)-(4-trifluoromethoxy-phenyl)-vinyl]-oxazol-4-ylmethoxy}-phenyl-methanesulfinyl)-ethyl]-1H[1,2,3]triazole in 25 ml dichloromethane. The mixture was stirred for 48 h and slowly allowed to reach room temperature. Additional 20 ml dichloromethane were added, washed with conc. sodium carbonate solution, water, dried and evaporated to give 29 mg (53%) of the title compound.

Workup

  1. customto reach room temperature
  2. washwashed with conc. sodium carbonate solution, water
  3. customdried
  4. customevaporated

Sources & evidence

ORD record
ord-5b36142630494e9a80413d7938df399d
Source dataset
uspto-grants-2006_02
Patent number
US07005526B2

Reaction notes

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