Carbon Tetrachloride → HCID 20220771, compound

HRID 980955Notes

Reaction equation

HRID 980955 reaction equation
[C:1]([Cl:5])(Cl)(Cl)Cl.ClCl.[C:8]([S:11][C:12]([S:34][C:35](=[O:37])[CH3:36])=[C:13]([N:27]1C(SC)[CH2:29][C:28]1=[O:33])[C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][CH:19]=1)=[O:15])(=[O:10])[CH3:9]>C(Cl)Cl>[C:8]([S:11][C:12]([S:34][C:35](=[O:37])[CH3:36])=[C:13]([N:27]1[CH:1]([Cl:5])[CH2:29][C:28]1=[O:33])[C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][CH:19]=1)=[O:15])(=[O:10])[CH3:9]

Participants

5

Reactant 3

HCID 5943Carbon TetrachlorideHCID 24526ChlorineHCID 20220836HCID 20220836, compound

Product 1

HCID 20220771HCID 20220771, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Following the procedure of Example 1(b), a carbon tetrachloride solution containing an equimolar amount of chlorine was added to a solution of p-nitrobenzyl 2-[bis(acetylthio)methylidene]-2-(4-methylthio-2-azetidinon-1-yl)acetate (144 mg, 0.306 mmole) in methylene chloride (2 ml) to give p-nitrobenzyl 2-[bis(acetylthio)methylidene]-2-(4chloro-2-azetidinon-1-yl)acetate. This crude 4-chloroazetidinone derivative was dissolved in methylene chloride (3 ml) and triethylamine (43 μl), and then 135 μl of a 30% methanol solution of methylamine were added thereto, after which the mixture was stirred for 15 minutes. The solvent was distilled off under reduced pressure. The residue was purified by column chromatography (eluent:ethyl acetate) to afford 60 mg of the desired compound.

Sources & evidence

ORD record
ord-d8ca830ca2704f279914f9a9be8ef40e
Source dataset
uspto-grants-1987_01
Patent number
US04639441

Reaction notes

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