Hydrochloric Acid → Methyl 3-(2-trichloroacetylpyrrol-1-yl)benzoate

HRID 399824Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 399824
[Cl:1][C:2]([Cl:7])([Cl:6])[C:3](Cl)=[O:4].[N:8]1([C:13]2[CH:14]=[C:15]([CH:20]=[CH:21][CH:22]=2)[C:16]([O:18][CH3:19])=[O:17])[CH:12]=[CH:11][CH:10]=[CH:9]1.N1C=CC=CC=1.Cl>ClCCCl.O.C(Cl)(Cl)Cl>[Cl:1][C:2]([Cl:7])([Cl:6])[C:3]([C:12]1[N:8]([C:13]2[CH:14]=[C:15]([CH:20]=[CH:21][CH:22]=2)[C:16]([O:18][CH3:19])=[O:17])[CH:9]=[CH:10][CH:11]=1)=[O:4]

Komponenten

8

Edukt 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 6420Trichloroacetyl chlorideHCID 3322314Methyl 3-(1H-pyrrol-1-yl)benzoate

Produkt 1

HCID 18945198Methyl 3-(2-trichloroacetylpyrrol-1-yl)benzoate

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 111,2-DichloroethaneLösungsmittelHCID 962WaterLösungsmittelHCID 6212ChloroformLösungsmittel

Versuchsvorschrift

Trichloroacetyl chloride (15.5 ml) was added to a mixture of methyl 3-(pyrrol-1-yl)benzoate (14.0 g) and pyridine (16.9 ml) in 1,2-dichloroethane (70 ml) under ice-cooling and the mixture was stirred for 7 days at ambient temperature. The mixture was poured into a mixture of chloroform and water, and the mixture was adjusted to pH 1 with 6N-hydrochloric acid. The separated organic layer was washed with a saturated aqueous sodium bicarbonate solution and water. The mixture was dried over magnesium sulfate and evaporated in vacuo. The residue was triturated with diisopropyl ether to give methyl 3-(2-trichloroacetylpyrrol-1-yl)benzoate (21.23 g).

Aufarbeitung

  1. temperaturecooling
  2. washThe separated organic layer was washed with a saturated aqueous sodium bicarbonate solution and water
  3. dry with materialThe mixture was dried over magnesium sulfate
  4. customevaporated in vacuo
  5. customThe residue was triturated with diisopropyl ether

Quellen und Nachweise

ORD-Eintrag
ord-8bfe52f7eaf74760a8571bf51d2959ac
Quelldatensatz
uspto-grants-1998_10
Patentnummer
US05824691

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