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(2-Nitrophenyl)acetic acid → 4,6-Dimethoxy-2-(2-nitrobenzyl)pyrimidine

HRID 1418813
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1418813
C(N(C(C)C)C(C)C)C.Cl.Cl.[C:12](=[NH:20])([O:18][CH3:19])[CH2:13][C:14](=[NH:17])[O:15][CH3:16].[N+:21]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[CH2:30][C:31](O)=O)([O-:23])=[O:22].C(C1NC=CN=1)(C1NC=CN=1)=O>ClCCl.CC(O)C>[CH3:16][O:15][C:14]1[CH:13]=[C:12]([O:18][CH3:19])[N:20]=[C:31]([CH2:30][C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=2[N+:21]([O-:23])=[O:22])[N:17]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 77337(2-Nitrophenyl)acetic acidHCID 81531DiisopropylethylamineHCID 5250894Bis-(1H-imidazol-2-YL)-methanoneHCID 12896693Dimethyl malonimidate dihydrochloride

Produkt 1

HCID 539772304,6-Dimethoxy-2-(2-nitrobenzyl)pyrimidineAusbeute 32,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3776
Isopropanol
Lösungsmittel
HCID 6344DichloromethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
-40 °C

Versuchsvorschrift

Ethyl diisopropylamine (240 ml) was added dropwise to a stirred suspension of dimethyl malonimidate dihydrochloride (73.2 g) in dichloromethane (400 ml) at -40° C. under nitrogen, and the mixture was stirred at -40° C. for 25 minutes to give suspension A. 2-Nitrophenylacetic acid (65.16 g) was added portionwise to a stirred suspension of carbonyl diimidazole (53.3 g) in dichloromethane (400 ml) at room temperature. The resulting solution was stirred for 10 minutes and was added dropwise over 30 minutes to the suspension A at -40° C. The mixture was stirred at -40° C. for a further 45 minutes and then at room temperature overnight, after which the solution was washed with water (400 ml), 2N HCl (400 ml) and saturated sodium bicarbonate solution (400 ml), dried and evaporated to give an orange solid. It was then stirred with propan-2-ol (50 ml) for 10 minutes and filtered. The solid was washed with a further 50 ml of propan-2 -ol and then dried to give 32.6 g of the desired product as a yellow solid, mp 92°-93° C.

Aufarbeitung

  1. customto give suspension A
  2. stirringThe resulting solution was stirred for 10 minutes
  3. additionwas added dropwise over 30 minutes to the suspension A at -40° C
  4. stirringThe mixture was stirred at -40° C. for a further 45 minutes
  5. washat room temperature overnight, after which the solution was washed with water (400 ml), 2N HCl (400 ml) and saturated sodium bicarbonate solution (400 ml)
  6. customdried
  7. customevaporated
  8. customto give an orange solid
  9. filtrationfiltered
  10. washThe solid was washed with a further 50 ml of propan-2 -ol
  11. customdried

Quellen und Nachweise

ORD-Eintrag
ord-0ad7c1e7889f4aeebb6e0c431b302659
Quelldatensatz
uspto-grants-1999_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05885935

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