Chlorine → HCID 20336570, compound

HRID 1706123Notes

Reaction equation

HRID 1706123 reaction equation
CS[CH:3]1[N:6]([CH2:7][C:8](=[O:15])[CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])[C:5](=[O:16])[CH2:4]1.[Cl:17]Cl>C(Cl)(Cl)(Cl)Cl>[Cl:17][CH:3]1[N:6]([CH2:7][C:8](=[O:15])[CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])[C:5](=[O:16])[CH2:4]1

Participants

4

Reactant 2

HCID 24526Chlorine2×HCID 20336571HCID 20336571, compound

Product 1

HCID 20336570HCID 20336570, compoundYield 105.6%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent2×

Procedure

Ethyl 4-(4-methylthio-2-oxoazetidin-1-yl)-3-oxobutyrate (400 mg, 1.63 mmole) was dissolved in dry carbon tetrachloride (15 ml) and the solution was stirred and ice-cooled while chlorine (115 mg, 1.6 mmmole) in carbon tetrachloride (1.4 ml) was added in one portion. After addition of the chlorine, the cooling bath was removed and stirring was continued for 3 minutes. The solvent was removed under reduced pressure to yield ethyl 4-(4-chloro-2-oxoazetidin-1-yl)-3-oxobutyrate as a pale yellow gum (400 mg), νmax (CHCl3): 1785 (β-lactam C=O), 1750 and 1730 (keto-ester C=O) cm-1.

Workup

  1. additionwas added in one portion
  2. customthe cooling bath was removed
  3. stirringstirring
  4. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-58160af9debd4aa480c9c8e370f396ea
Source dataset
uspto-grants-1980_06
Patent number
US04206120

Reaction notes

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