Sulfuryl chloride → HCID 86741247, compound

HRID 980957Notes

Reaction equation

HRID 980957 reaction equation
S(Cl)([Cl:4])(=O)=O.CS[CH:8]1[N:11]([C:12](=[C:17]2[S:21][C:20]([C:23]([F:26])([F:25])[F:24])([OH:22])[CH2:19][S:18]2)[C:13]([O:15][CH3:16])=[O:14])[C:10](=[O:27])[CH2:9]1>C(Cl)Cl>[Cl:4][CH:8]1[N:11]([C:12](=[C:17]2[S:21][C:20]([C:23]([F:26])([F:25])[F:24])([OH:22])[CH2:19][S:18]2)[C:13]([O:15][CH3:16])=[O:14])[C:10](=[O:27])[CH2:9]1

Participants

4

Reactant 2

HCID 24648Sulfuryl chlorideHCID 53809511HCID 53809511, compound

Product 1

HCID 86741247HCID 86741247, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Sulphuryl chloride (59.7 mg, 35.8 μl, 0.442 mmole) was added to a solution of methyl 2-(4-methylthio-2-azetidinon-1-yl)-2-(4-trifluoromethyl-4-hydroxy-1,3-dithiolan-2-ylidene)acetate (166 mg, 0.442 mmole) in methylene chloride (3 ml) at room temperature, with stirring. After this addition, the solution was stirred for 3 minutes and then the solvent was distilled off to give the crude methyl 2-(4-chloro-2-azetidinon-1-yl)-2-(4-trifluoromethyl-4-hydroxy-1,3-dithiolan-2-ylidene)acetate. This 4-chloroazetidinone compound was dissolved in methylene chloride (3 ml) without purification, and triethylamine (185 μl) was added thereto, after which the mixture was stirred at room temperature for 2 hours. The solvent was distilled off from the reaction mixture under reduced pressure. The resulting residue was dissolved in ethyl acetate and washed with an aqueous solution of sodium chloride and dried over anhydrous sodium sulphate. The solvent was distilled off under reduced pressure and the residue was purified by preparative thin layer chromatography (eluent: a 3:2 by volume mixture of benzene and ethyl acetate), to give 63 mg of the desired product as crystals.

Workup

  1. additionAfter this addition
  2. stirringthe solution was stirred for 3 minutes
  3. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-2cca49aed6584d578a5547d53309608b
Source dataset
uspto-grants-1987_01
Patent number
US04639441

Reaction notes

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