m-Chloroperbenzoic acid → 1-methanesulphonyl-hexahydro-4,5-epoxy-1H-azepine

HRID 1389852Notes

Reaction equation

HRID 1389852 reaction equation
[CH3:1][S:2]([N:5]1[CH2:11][CH2:10][CH:9]=[CH:8][CH2:7][CH2:6]1)(=[O:4])=[O:3].ClC1C=CC=C(C(OO)=[O:20])C=1>C(Cl)Cl>[CH3:1][S:2]([N:5]1[CH2:6][CH2:7][CH:8]2[O:20][CH:9]2[CH2:10][CH2:11]1)(=[O:4])=[O:3]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 13192285HCID 13192285, compound

Product 1

HCID 205489081-methanesulphonyl-hexahydro-4,5-epoxy-1H-azepine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

11.7 g (0.067 mol) of 1-methanesulphonyl-2,3,6,7-tetrahydro-1H-azepine are dissolved in 230 ml of methylene chloride and the solution is treated with 23 g (0.13 mol) of m-chloro-perbenzoic acid in portions. A white suspension soon forms and this is stirred for a further 24 hours at room temperature. The m-chlorobenzoic acid which has precipitated is filtered off and the filtrate is washed with a saturated aqueous solution of sodium carbonate, then with aqueous iron-II sulphate solution, then with 0.1 N sodium hydroxide solution and finally with water and dried over sodium sulphate. On concentrating the solution under a water pump vacuum, while crystals of 1-methanesulphonyl-hexahydro-4,5-epoxy-1H-azepine are obtained and these are isolated by filtration; melting point 133°-134°.

Workup

  1. customThe m-chlorobenzoic acid which has precipitated
  2. filtrationis filtered off
  3. washthe filtrate is washed with a saturated aqueous solution of sodium carbonate
  4. dry with materialwith aqueous iron-II sulphate solution, then with 0.1 N sodium hydroxide solution and finally with water and dried over sodium sulphate
  5. concentrationOn concentrating the solution under a water pump vacuum

Sources & evidence

ORD record
ord-83987eeac2794123ba04aaeca279aaca
Source dataset
uspto-grants-1981_01
Patent number
US04246269

Reaction notes

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