m-Chloroperbenzoic acid → HCID 11649304, compound

HRID 892254Notes

Reaction equation

HRID 892254 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][C:3]=1/[CH:12]=[CH:13]/[C:14]1[O:15][CH:16]=[C:17]([CH2:19][O:20][C:21]2[CH:35]=[CH:34][C:24]([CH2:25][S:26][CH2:27][CH2:28][N:29]3[CH:33]=[CH:32][N:31]=[N:30]3)=[CH:23][CH:22]=2)[N:18]=1.ClC1C=C(C(OO)=[O:44])C=CC=1>ClCCl.C(OCC)(=O)C>[F:1][C:2]1[CH:7]=[C:6]([C:8]([F:10])([F:9])[F:11])[CH:5]=[CH:4][C:3]=1/[CH:12]=[CH:13]/[C:14]1[O:15][CH:16]=[C:17]([CH2:19][O:20][C:21]2[CH:35]=[CH:34][C:24]([CH2:25][S:26]([CH2:27][CH2:28][N:29]3[CH:33]=[CH:32][N:31]=[N:30]3)=[O:44])=[CH:23][CH:22]=2)[N:18]=1

Participants

5

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 11497053HCID 11497053, compound

Product 1

HCID 11649304HCID 11649304, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
30 °C

Procedure

To a solution of 101 mg (0.20 mmol) 1-[2-(4-{2-[2-(E)-(2-fluoro-4-trifluoromethylphenyl)-vinyl]-oxazol-4-ylmethoxy}-benzylsulfanyl)-ethyl]-1H-[1,2,3]triazole in 8 ml dichloromethane at −30° C. were added drop by drop during 20 min 54 mg (0.24 mmol) 3-chloro-benzenecarboperoxoic acid dissolved in 2 ml ethyl acetate. After 1 hour stirring at 30° C. the mixture was allowed to warm up over night, diluted with dichloromethane, washed with sodium bicarbonate solution, then with water, dried and evaporated. Elution from silica with ethyl acetate/methanol 9:1 furnished 73 mg (71%) title compound as white solid.

Workup

  1. temperatureto warm up over night
  2. washwashed with sodium bicarbonate solution
  3. dry with materialwith water, dried
  4. customevaporated
  5. washElution from silica with ethyl acetate/methanol 9:1

Sources & evidence

ORD record
ord-46e6ab0ddc374121b6f76b751de74ba6
Source dataset
uspto-grants-2006_02
Patent number
US07005526B2

Reaction notes

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