m-Chloroperbenzoic acid → HCID 11656522, compound

HRID 892248Notes

Reaction equation

HRID 892248 reaction equation
[F:1][C:2]([F:35])([F:34])[O:3][C:4]1[CH:9]=[CH:8][C:7](/[CH:10]=[CH:11]/[C:12]2[O:13][CH:14]=[C:15]([CH2:17][O:18][C:19]3[CH:33]=[CH:32][C:22]([CH2:23][S:24][CH2:25][CH2:26][N:27]4[CH:31]=[CH:30][N:29]=[N:28]4)=[CH:21][CH:20]=3)[N:16]=2)=[CH:6][CH:5]=1.ClC1C=C(C(OO)=[O:44])C=CC=1>ClCCl.C(OCC)(=O)C>[F:35][C:2]([F:1])([F:34])[O:3][C:4]1[CH:5]=[CH:6][C:7](/[CH:10]=[CH:11]/[C:12]2[O:13][CH:14]=[C:15]([CH2:17][O:18][C:19]3[CH:33]=[CH:32][C:22]([CH2:23][S:24]([CH2:25][CH2:26][N:27]4[CH:31]=[CH:30][N:29]=[N:28]4)=[O:44])=[CH:21][CH:20]=3)[N:16]=2)=[CH:8][CH:9]=1

Participants

5

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 11562433HCID 11562433, compound

Product 1

HCID 11656522HCID 11656522, compoundYield 74.3%

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)-(4-trifluoromethoxy-phenyl)vinyl]-oxazol-4-ylmethoxy}-benzylsulfanyl)-ethyl]-1H-[1,2,3]triazole in 8 ml dichloromethane at −30° C. were added dropwise 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 77 mg (74%) title compound as off-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-30ba8f5b3c0a46f0be7616bbf33ff469
Source dataset
uspto-grants-2006_02
Patent number
US07005526B2

Reaction notes

Loading…