m-Chloroperbenzoic acid → HCID 21452939, compound

HRID 436664Notes

Reaction equation

HRID 436664 reaction equation
[CH2:1]([NH:22][C:23](=[O:35])[C:24]1[CH:29]=[CH:28][C:27]([O:30][C:31]([F:34])([F:33])[F:32])=[CH:26][CH:25]=1)[CH2:2]/[CH:3]=[CH:4]/[CH2:5][CH2:6][CH2:7][NH:8][C:9](=[O:21])[C:10]1[CH:15]=[CH:14][C:13]([O:16][C:17]([F:20])([F:19])[F:18])=[CH:12][CH:11]=1.ClC1C=CC=C(C(OO)=[O:44])C=1>C(Cl)(Cl)Cl>[O:44]1[CH:4]([CH2:3][CH2:2][CH2:1][NH:22][C:23](=[O:35])[C:24]2[CH:25]=[CH:26][C:27]([O:30][C:31]([F:32])([F:33])[F:34])=[CH:28][CH:29]=2)[CH:5]1/[CH:6]=[CH:7]/[NH:8][C:9](=[O:21])[C:10]1[CH:11]=[CH:12][C:13]([O:16][C:17]([F:19])([F:20])[F:18])=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 21452876HCID 21452876, compound

Product 1

HCID 21452939HCID 21452939, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
3 °C

Procedure

To a stirred and chilled (3° C., kept in an ice bath) solution containing N,N'-(trans-3-heptene-1,7-diyl)bis(4-trifluoromethoxybenzamide) dissolved in 300 ml. of chloroform was added in one portion 7.2 g. of 3-chloroperbenzoic acid. The reaction mixture was stirred for an additional 30 minutes at 3°-5° C. and then was allowed to stand at 5° C. for an additional 42 hours. The reaction mixture was then washed successively with three 50 ml. portions of cold 5% aqueous potassium carbonate solution and next with saturated brine, and then it was dried over anhydrous potassium carbonate. The solvent was distilled off in vacuo and the remaining white solid was recrystallized from benzene-ethanol to yield 7.75 g. of N,N'-(trans-3,4-epoxyheptane-1,7-diyl)bis( 4-trifluoromethoxybenzamide), m.p. 121°-123° C.

Workup

  1. dissolutiondissolved in 300 ml
  2. stirringThe reaction mixture was stirred for an additional 30 minutes at 3°-5° C.
  3. washThe reaction mixture was then washed successively with three 50 ml
  4. dry with materialportions of cold 5% aqueous potassium carbonate solution and next with saturated brine, and then it was dried over anhydrous potassium carbonate
  5. distillationThe solvent was distilled off in vacuo
  6. customthe remaining white solid was recrystallized from benzene-ethanol
  7. customto yield 7.75 g

Sources & evidence

ORD record
ord-e5b43461b56241aea9abd83891a7772e
Source dataset
uspto-grants-1977_02
Patent number
US04009208

Reaction notes

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