Bromoacetyl bromide → HCID 13457766, Verbindung

HRID 280138Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 280138
[Cl:1][C:2]1[CH:17]=[CH:16][CH:15]=[CH:14][C:3]=1[C:4]([C:6]1[N:7]([NH:12][CH3:13])[C:8]([CH3:11])=[CH:9][CH:10]=1)=[O:5].C(=O)(O)[O-].[Na+].[Br:23][CH2:24][C:25](Br)=[O:26]>ClCCl>[CH3:13][N:12]([N:7]1[C:8]([CH3:11])=[CH:9][CH:10]=[C:6]1[C:4](=[O:5])[C:3]1[CH:14]=[CH:15][CH:16]=[CH:17][C:2]=1[Cl:1])[C:25](=[O:26])[CH2:24][Br:23]

Komponenten

5

Edukt 3

HCID 61147Bromoacetyl bromideHCID 516892Sodium BicarbonateHCID 13457765HCID 13457765, Verbindung

Produkt 1

HCID 13457766HCID 13457766, VerbindungAusbeute 82 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A stirred slurry of 2-(2-chlorobenzoyl)-1-methylamino-5-methylpyrrole (18.7 g, 75 mmol) and sodium bicarbonate (14.2 g, 170 mmol) in 100 ml of dichloromethane was treated with a solution of bromoacetyl bromide (15.2 g, 90 mmol) in 30 ml of dichloromethane over 30 minutes and stirred at room temperature ovrnight. The reaction mixture was quenched with 100 ml of H2O, separated, washed with H2O and brine, dried (MgSO4), filtered, and evaporated. The resultant oil was purified by HPLC (silica, 1:1 ethyl acetate-hexane) to give an oil which crystallized from ether to give 22.7 g (82%) of needles, m.p. 108°-109°.

Aufarbeitung

  1. customThe reaction mixture was quenched with 100 ml of H2O
  2. customseparated
  3. washwashed with H2O and brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated
  7. customThe resultant oil was purified by HPLC (silica, 1:1 ethyl acetate-hexane)
  8. customto give an oil which
  9. customcrystallized from ether

Quellen und Nachweise

ORD-Eintrag
ord-abb1fb7b66c34f0b80b2eb5d6b968035
Quelldatensatz
uspto-grants-1986_05
Patentnummer
US04588727

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