Ethyl chloroformate → HCID 13457750, Verbindung

HRID 462748Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 462748
[NH2:1][N:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[C:7](=[O:15])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[Cl:14].C(=O)(O)[O-].[Na+].Cl[C:22]([O:24][CH2:25][CH3:26])=[O:23]>ClCCl>[Cl:14][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=1[C:7]([C:3]1[N:2]([NH:1][C:22](=[O:23])[O:24][CH2:25][CH3:26])[CH:6]=[CH:5][CH:4]=1)=[O:15]

Komponenten

5

Edukt 3

HCID 10928Ethyl chloroformateHCID 516892Sodium BicarbonateHCID 13457740HCID 13457740, Verbindung

Produkt 1

HCID 13457750HCID 13457750, VerbindungAusbeute 120,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

1-Amino-2-(2-chlorobenzoyl)pyrrole (32 g, 0.145 mol) was combined with sodium bicarbonate (30.2 g, 0.36 mol) in 400 ml of dichloromethane. To this rapidly stirred mixture was added ethyl chloroformate (18.6 g, 0.172 mol) over 2 minutes and the resultant slurry heated under reflux for 2.5 hours. The reaction mixture was quenched with 300 ml of H2O, separated, washed with H2O, dried (MgSO4), filtered, and evaporated to give 51 g of an oil. This oil was purified by HPLC (silica, 10:1 DCM-ethyl acetate) to give after evaporation 32.8 g (77%) of crystals, m.p. 90°-92°.

Aufarbeitung

  1. temperaturethe resultant slurry heated
  2. temperatureunder reflux for 2.5 hours
  3. customThe reaction mixture was quenched with 300 ml of H2O
  4. customseparated
  5. washwashed with H2O
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-a99b720a5ded444b9585e9e8f2e0ec43
Quelldatensatz
uspto-grants-1985_05
Patentnummer
US04517195

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