Chlorine → HCID 20336569, compound

HRID 1706124Notes

Reaction equation

HRID 1706124 reaction equation
CS[CH:3]1[N:6]([CH2:7][C:8](=[O:15])[CH:9]([CH3:14])[C:10]([O:12][CH3:13])=[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])[CH:9]([CH3:14])[C:10]([O:12][CH3:13])=[O:11])[C:5](=[O:16])[CH2:4]1

Participants

4

Reactant 2

HCID 24526Chlorine2×HCID 20336618HCID 20336618, compound

Product 1

HCID 20336569HCID 20336569, compoundYield 104.2%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent2×

Procedure

Methyl 4-(4-methylthio-2-oxoazetidin-1-yl)-2-methyl-3-oxobutyrate (280 mg, 1.14 mmole) was dissolved in dry carbon tetrachloride (15 ml) and to the stirred ice-cooled solution chlorine (80 mg, 1.13 mmole) in carbon tetrachloride (3.2 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 evaporated under reduced pressure to yield methyl 4-(4-chloro-2-oxoazetidin-1-yl)-2-methyl-3-oxobutyrate as a pale yellow gum (275 mg). νmax (CHCl3): 1780 (β-lactam C=O), 1755 (ester C=O), 1725 (ketone C=O) cm-1.

Workup

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

Sources & evidence

ORD record
ord-b065768768a849a8a438ffead1891965
Source dataset
uspto-grants-1980_06
Patent number
US04206120

Reaction notes

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