1,2-Dichloroethane → HCID 86734481, compound

HRID 436031Notes

Reaction equation

HRID 436031 reaction equation
[CH3:1][O:2][C:3]([CH:5]([N:9]1[CH:12]([S:13][N:14]2[C:18](=[O:19])[CH2:17][CH2:16][C:15]2=[O:20])[CH:11]([NH:21][C:22](=[O:30])[CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:10]1=[O:31])[C:6]([CH3:8])=[CH2:7])=[O:4].C1OC1C.[Br:36]N1C(=O)CCC1=O.ClCCCl>C(Cl)(Cl)(Cl)Cl>[CH3:1][O:2][C:3]([CH:5]([N:9]1[CH:12]([S:13][N:14]2[C:18](=[O:19])[CH2:17][CH2:16][C:15]2=[O:20])[CH:11]([NH:21][C:22](=[O:30])[CH2:23][C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[C:10]1=[O:31])[C:6]([CH2:8][Br:36])=[CH2:7])=[O:4]

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 6378Propylene OxideHCID 67184N-bromobutanimideHCID 86733532HCID 86733532, compound

Product 1

HCID 86734481HCID 86734481, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
76 °C

Procedure

A mixture of 4.45 g (10 mmoles) of 1-(1-methoxycarbonyl-2-methylprop-2-enyl)-3-phenylacetamido-4-succinimidothio-azetidin-2-one, 10 ml of propylene oxide, 3.6 g (20 mmoles) of N-bromosuccinimide, 50 mg of azo-isobutyronitrile, 100 ml of 1,2dichloroethane and 200 ml of carbon tetrachloride was heated for 5 hours at 76° C under nitrogen. After washing with sodium metabisulfite and water, the reaction mixture was concentrated and purified by column chromatography [silica gel; toluene-ethyl acetate 3:1 (v/v)] to obtain 1-(1-methoxycarbonyl-2-bromomethylprop-2-enyl)-3-phenylacetamido-4-succinimidothio-azetidin-2-one. The structure was confirmed by PMR and IR spectroscopy.

Workup

  1. washAfter washing with sodium metabisulfite and water
  2. concentrationthe reaction mixture was concentrated
  3. custompurified by column chromatography [silica gel; toluene-ethyl acetate 3:1 (v/v)]

Sources & evidence

ORD record
ord-5ea7d8431c494175b207d4d9c93ab98a
Source dataset
uspto-grants-1977_02
Patent number
US04007202

Reaction notes

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