Hydrochloric Acid → HCID 20469133, compound

HRID 1388932Notes

Reaction equation

[CH3:1][N:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[Cl:7].[CH3:8][N:9]1[C:13]([C:14](Cl)=[O:15])=[C:12]([CH3:17])[CH:11]=[C:10]1[CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20].Cl[Sn](Cl)(Cl)Cl.Cl>C(Cl)Cl>[CH3:8][N:9]1[C:13]([C:14]([C:6]2[N:2]([CH3:1])[C:3]([Cl:7])=[CH:4][CH:5]=2)=[O:15])=[C:12]([CH3:17])[CH:11]=[C:10]1[CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20]

Participants

Conditions

Temperature: 0 °C

Procedure

1-Methyl-2-chloropyrrole (5.83 g, 0.05 mole) and ethyl 1,4-dimethyl-5-chlorocarbonylpyrrole-2-acetate (11.5 g, 0.05 mole) are dissolved in 25 ml methylene chloride and stirred under nitrogen atmosphere at 0° C. Thirteen grams (0.05 mole) of SnCl4 in 10 ml methylene chloride is added slowly to the vigorously stirred solution. The resulting orange-brown mixture is stirred at 0° C. for 30 minutes then at room temp. for 3 hours. At the end of this period, 20 ml of 6 N HCl is added and stirred for 30 minutes. The mixture is extracted three times with 100 ml portions of methylene chloride and the crude product is purified by column chromatography and recrystallized from ether/petroleum ether to afford 9.5 g (63% yield) of ethyl 1,4-dimethyl-5-(1-methyl-5'-chloropyrrol-2-oyl)pyrrole-2-acetate.

Workup

stirringThe resulting orange-brown mixture is stirred at 0° C. for 30 minutes
stirringstirred for 30 minutes
extractionThe mixture is extracted three times with 100 ml portions of methylene chloride
customthe crude product is purified by column chromatography
customrecrystallized from ether/petroleum ether

Sources & evidence

ORD record: ord-5b0214b6b812418ab75f67e960b270d8
Source dataset: uspto-grants-1984_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04434175

Reaction notes

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