m-Chloroperbenzoic acid → HCID 11627975, compound

HRID 892263Notes

Reaction equation

HRID 892263 reaction equation
[CH3:1][C:2]1[CH:16]=[C:15]([O:17][CH2:18][C:19]2[N:20]=[C:21](/[CH:24]=[CH:25]/[C:26]3[CH:31]=[CH:30][C:29]([C:32]([F:35])([F:34])[F:33])=[CH:28][C:27]=3[F:36])[O:22][CH:23]=2)[CH:14]=[CH:13][C:3]=1[CH2:4][S:5][CH2:6][CH2:7][N:8]1[CH:12]=[CH:11][N:10]=[N:9]1.ClC1C=C(C(OO)=[O:45])C=CC=1>ClCCl.C(OCC)(=O)C>[F:36][C:27]1[CH:28]=[C:29]([C:32]([F:34])([F:33])[F:35])[CH:30]=[CH:31][C:26]=1/[CH:25]=[CH:24]/[C:21]1[O:22][CH:23]=[C:19]([CH2:18][O:17][C:15]2[CH:14]=[CH:13][C:3]([CH2:4][S:5]([CH2:6][CH2:7][N:8]3[CH:12]=[CH:11][N:10]=[N:9]3)=[O:45])=[C:2]([CH3:1])[CH:16]=2)[N:20]=1

Participants

5

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 11577208HCID 11577208, compound

Product 1

HCID 11627975HCID 11627975, compoundYield 46.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-30 °C

Procedure

To a solution of 650 mg (1.25 mmol) 1-[2-(2-methyl-4-{2-[2-(E)-(2-fluoro-4-trifluoromethyl-phenyl)-vinyl]-oxazol-4-ylmethoxy}-benzylsulfanyl)-ethyl]-1H[1,2,3]triazole in 35 ml dichloromethane at −30° C. were added dropwise during 20 min. 493 mg (2.20 mmol) 3-chloro-benzenecarboperoxoic acid (77% peracid) dissolved in 20 ml ethyl acetate. After 1 hour stirring at −30° C. the mixture was allowed to warm up over night, stirred another 48 hours at room temperature, diluted with dichloromethane, washed with sodium bicarbonate solution, then with water, dried and evaporated. Elution from silica with ethyl acetate (1–10% methanol gradient) furnished as the second fraction 310 mg (46%) title compound as white solid.

Workup

  1. temperatureto warm up over night
  2. stirringstirred another 48 hours at room temperature
  3. washwashed with sodium bicarbonate solution
  4. dry with materialwith water, dried
  5. customevaporated
  6. washElution from silica with ethyl acetate (1–10% methanol gradient)

Sources & evidence

ORD record
ord-909f8dd8100c47fd9cc9402ace328dc8
Source dataset
uspto-grants-2006_02
Patent number
US07005526B2

Reaction notes

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