Triethylamine → Isopropyl 2-chloro-5-[(2,4,5-trimethylfuran-3-carbonyl)amino]benzoate

HRID 326338

Reaktionsgleichung

Reaktionsgleichung von HRID 326338
[CH3:1][C:2]1[O:3][C:4]([CH3:11])=[C:5]([CH3:10])[C:6]=1[C:7](Cl)=[O:8].[NH2:12][C:13]1[CH:14]=[CH:15][C:16]([Cl:25])=[C:17]([CH:24]=1)[C:18]([O:20][CH:21]([CH3:23])[CH3:22])=[O:19].C(N(CC)CC)C>C1(C)C=CC=CC=1>[Cl:25][C:16]1[CH:15]=[CH:14][C:13]([NH:12][C:7]([C:6]2[C:5]([CH3:10])=[C:4]([CH3:11])[O:3][C:2]=2[CH3:1])=[O:8])=[CH:24][C:17]=1[C:18]([O:20][CH:21]([CH3:23])[CH3:22])=[O:19]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 369590Isopropyl 5-amino-2-chlorobenzoateHCID 145359342,4,5-Trimethyl-3-furancarbonyl chloride

Produkt 1

HCID 507312Isopropyl 2-chloro-5-[(2,4,5-trimethylfuran-3-carbonyl)amino]benzoateAusbeute 42,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel2×

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

A solution of 2,4,5-trimethyl-3-furancarbonyl chloride (7.8 g, 0.045 mole) in toluene (25 ml) was added to 1-methylethyl 5-amino-2-chlorobenzoate (10.6 g, 0.050 mole) and triethylamine (6 g) in toluene (25 ml). The mixture was warmed to 60° C. for about 1 hour, then washed in sequence with dilute hydrochloric acid, water, aqueous 5% sodium bicarbonate and water. The solution was dried with magnesium sulfate, filtered and evaporated. The residue was crystallized from toluene/petroleum ether to give 6.7 g of a pale yellow solid, m.p. 83°-85° C.

Aufarbeitung

  1. washwashed in sequence with dilute hydrochloric acid, water, aqueous 5% sodium bicarbonate and water
  2. dry with materialThe solution was dried with magnesium sulfate
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue was crystallized from toluene/petroleum ether

Quellen und Nachweise

ORD-Eintrag
ord-75503f14faa44da6902649854861f5a8
Quelldatensatz
uspto-grants-1993_12
Patentnummer
US05268389

Verknüpfte Notizen

Wird geladen…