1,2-Dichloroethane → N-(1-methylethyl)-3-phenyl-2-oxiranecarboxamide

HRID 1759518Notes

Reaction equation

HRID 1759518 reaction equation
[CH3:1][CH:2]([NH:4][C:5]([C:7](=O)C=CC1C=CC=CC=1)=[O:6])[CH3:3].Cl[C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([O:26]O)=O)[CH:19]=1.S(C1C(C)=CC(O)=C(C(C)(C)C)C=1)C1C(C)=CC(O)=C(C(C)(C)C)C=1.C(Cl)CCl>C(Cl)(Cl)Cl>[CH3:1][CH:2]([NH:4][C:5]([CH:7]1[CH:24]([C:20]2[CH:19]=[CH:18][CH:23]=[CH:22][CH:21]=2)[O:26]1)=[O:6])[CH3:3]

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 7308SantonoxHCID 70297m-Chloroperbenzoic acidHCID 3770630N-(1-methylethyl)cinnamoylcarboxamide

Product 1

HCID 13041334N-(1-methylethyl)-3-phenyl-2-oxiranecarboxamide

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of N-(1-methylethyl)cinnamoylcarboxamide (18 g.), m-chloroperbenzoic acid (23.6 g.), 4,4'-thiobis(6-tert-butyl-m-cresol) (0.3 g.) and ethylene dichloride (250 ml.) was heated under gentle reflux for 1 hour, then chilled in ice. A precipitate (m-chlorobenzoic acid) was separated by filtration and washed with ethylene dichloride. The filtrate and washings were combined, and evaporated under reduced pressure on a rotary evaporator to give an amber oil. The oil was dissolved in chloroform (300 ml.) and the chloroform solution was washed with 5% aqueous sodium bicarbonate solution twice, then with saline. The chloroform solution was dried over magnesium sulfate, then evaporated under reduced pressure in a rotary evaporator to give an oil. The oil solidified on standing. The solid mass was recrystallized from ether giving 8.4 g. of product, m.p. 114°-115°.

Workup

  1. temperaturewas heated
  2. temperatureunder gentle reflux for 1 hour
  3. temperaturechilled in ice
  4. customA precipitate (m-chlorobenzoic acid) was separated by filtration
  5. washwashed with ethylene dichloride
  6. customevaporated under reduced pressure on a rotary evaporator
  7. customto give an amber oil
  8. washthe chloroform solution was washed with 5% aqueous sodium bicarbonate solution twice
  9. dry with materialThe chloroform solution was dried over magnesium sulfate
  10. customevaporated under reduced pressure in a rotary evaporator
  11. customto give an oil
  12. customThe solid mass was recrystallized from ether giving 8.4 g

Sources & evidence

ORD record
ord-ee5e9b5c6fec48fa966cd48fedad834c
Source dataset
uspto-grants-1982_07
Patent number
US04341718

Reaction notes

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