Hydrochloric Acid → HCID 13013929, compound

Reaction equation

CCOCC.Cl.Cl[C:8]1[C:14]2[CH:15]=[CH:16][C:17]([C:19]([O:21][CH3:22])=[O:20])=[CH:18][C:13]=2[S:12][C:11]2[CH:23]=[CH:24][CH:25]=[CH:26][C:10]=2[N:9]=1>C(Cl)Cl>[CH:15]1[C:14]2[CH:8]=[N:9][C:10]3[CH:26]=[CH:25][CH:24]=[CH:23][C:11]=3[S:12][C:13]=2[CH:18]=[C:17]([C:19]([O:21][CH3:22])=[O:20])[CH:16]=1

Participants

Procedure

Stir at room temperature a mixture of 4.27 gm. (22.54 mmole) of stannous chloride in 200 ml. of dry ether while passing dry hydrogen chloride through the mixture to saturation. Dissolve 3.42 gm. (11.27 mmole) of the 11-chloro ester of Example 6 in 35 ml. of methylene chloride and add this solution to the stannous chloride solution over a 10 minute period. Pass dry hydrogen chloride through the mixture for 30 minutes and decant the supernatant liquid. Wash the residue by decantation with dry ether. Filter and wash with dry ether. Shake the solids for 2 minutes in a mixture of 25 ml. of 5 N aqueous sodium hydroxide and 25 ml. of methylene chloride. Separate the organic layer and extract the aqueous layer with 25 ml. of methylene chloride. Wash the combined extracts with water, separate the organic layer and dry over magnesium sulfate. Evaporate to a residue. Recrystallize from acetonitrile to obtain the title product, (m.p. 103.5°-109.5° C.).