Oxalyl chloride → p-Nitrobenzyl 2-(4-chloro-2-oxo-1-azetidinyl)-3-acetylthio-3-(2-ethoxyethylthio)acrylate

HRID 4435Notes

Reaction equation

HRID 4435 reaction equation
C(S([CH:5]1[N:8]([C:9](=[C:23]([S:30][C:31](=[O:33])[CH3:32])[S:24][CH2:25][CH2:26][O:27][CH2:28][CH3:29])[C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=2)=[O:11])[C:7](=[O:34])[CH2:6]1)=O)C.C(Cl)(=O)C([Cl:38])=O>C(Cl)Cl>[Cl:38][CH:5]1[N:8]([C:9](=[C:23]([S:30][C:31](=[O:33])[CH3:32])[S:24][CH2:25][CH2:26][O:27][CH2:28][CH3:29])[C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=2)=[O:11])[C:7](=[O:34])[CH2:6]1

Participants

4

Reactant 2

HCID 65578Oxalyl chlorideHCID 53818988p-Nitrobenzyl 2-(4-ethylsulfinyl-2-oxo-1-azetidinyl)-3-acetylthio-3-(2-ethoxyethylthio)acrylate

Product 1

HCID 54496834p-Nitrobenzyl 2-(4-chloro-2-oxo-1-azetidinyl)-3-acetylthio-3-(2-ethoxyethylthio)acrylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1.2 g p-nitrobenzyl 2-(4-ethylsulfinyl-2-oxo-1-azetidinyl)-3-acetylthio-3-(2-ethoxyethylthio)-acrylate in 50 ml methylene chloride was cooled to -50° C. under a nitrogen atmosphere. Oxalyl chloride (0.196 ml) was added dropwise at -50° C., then the reaction mixture was allowed to warm to -15°. After 1 hour at -15° C. the methylene chloride solution was washed with 20 ml saturated aqueous sodium bicarbonate solution and 20 ml water, dried over anhydrous sodium sulfate and concentratedd in vacuo to an oil (1.2 g). The crude title compound was used without further purification. The NMR spectrum of a deuterochloroform solution showed peaks at 1.23(, 3H); 2.3-3.72(c, 11H); 5.23 (m, 2H); 5.7-6.32(c, 1H); 7.52(m, 2H); and 8.2(m, 2H) ppm. The infrared spectrum of a chloroform solution had absorption bands at 5.6 and 5.78 microns.

Workup

  1. temperatureto warm to -15°
  2. washAfter 1 hour at -15° C. the methylene chloride solution was washed with 20 ml saturated aqueous sodium bicarbonate solution and 20 ml water
  3. dry with materialdried over anhydrous sodium sulfate and concentratedd in vacuo to an oil (1.2 g)
  4. customThe crude title compound was used without further purification
  5. customabsorption bands at 5.6 and 5.78 microns

Sources & evidence

ORD record
ord-869be1612db248ec8bde7c16dc757fd7
Source dataset
uspto-grants-1988_02
Patent number
US04725678

Reaction notes

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