4,6-Dichloro-5-nitropyrimidine → HCID 178526808, Verbindung

HRID 262118

Reaktionsgleichung

Reaktionsgleichung von HRID 262118
ClC1C([N+]([O-])=O)=C(Cl)N=CN=1.Cl.[Cl:13][CH2:14][CH2:15][NH2:16].C(=O)(O)[O-].[Na+].Cl[CH2:23][CH2:24][NH:25][C:26]1[C:31]([N+:32]([O-:34])=[O:33])=[C:30](Cl)[N:29]=[CH:28][N:27]=1.[N+](C1C(CCCl)=NC=NC=1CCCl)([O-])=O>CCOCC.C(Cl)(Cl)Cl>[Cl:13][CH2:14][CH2:15][NH:16][C:30]1[N:29]=[CH:28][N:27]2[CH2:23][CH2:24][N:25]=[C:26]2[C:31]=1[N+:32]([O-:34])=[O:33]

Komponenten

8

Edukt 5

HCID 203124,6-Dichloro-5-nitropyrimidineHCID 516892Sodium BicarbonateHCID 97937372-Chloroethylamine hydrochlorideHCID 213200775-Nitro-4,6-bis(beta-chloroethyl)pyrimidineHCID 213201124-(beta-Chloroethylamino)-5-nitro-6-chloropyrimidine

Produkt 1

HCID 178526808HCID 178526808, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 6212ChloroformLösungsmittel

Versuchsvorschrift

A solution of 20 g. of 4,6-dichloro-5-nitropyrimidine was prepared in ether. An aqueous solution containing 14 g. of β-chloroethylamine hydrochloride and 24 g. of sodium bicarbonate were added thereto and the subsequent mixture agitated for about 30 minutes. The ether layer was separated, and the separated layer washed with water and dried. Removal of the ether in vacuo yielded an oil containing chiefly 4-(β-chloroethylamino)-5-nitro-6-chloropyrimidine plus a small quantity of 5-nitro-4,6-bis(β-chloroethyl)pyrimidine (the disubstituted product) and a very small quantity of starting material. The oily residue was allowed to stand in chloroform for about one day. A solid comprising 7-(β-chloroethylamino)-8-nitro-2,3-dihydroimidazo[1,2-c]pyrimidine hydrochloride precipitated and the precipitate was separated by filtration, 7-(β-chloroethyl)amino-8-nitro-2,3-dihydroimidazo[1,2-c]pyrimidine hydrochloride thus prepared decomposed at 135° C. after recrystallization from chloroform; yield=5.378 g.

Aufarbeitung

  1. additionAn aqueous solution containing 14 g
  2. customThe ether layer was separated
  3. washthe separated layer washed with water
  4. customdried
  5. customRemoval of the ether in vacuo
  6. customyielded an oil
  7. customA solid comprising 7-(β-chloroethylamino)-8-nitro-2,3-dihydroimidazo[1,2-c]pyrimidine hydrochloride precipitated
  8. customthe precipitate was separated by filtration, 7-(β-chloroethyl)amino-8-nitro-2,3-dihydroimidazo[1,2-c]pyrimidine hydrochloride
  9. customthus prepared
  10. customdecomposed at 135° C.
  11. customafter recrystallization from chloroform

Quellen und Nachweise

ORD-Eintrag
ord-a6cb9de849fe45bd9d458bc5c047d3d7
Quelldatensatz
uspto-grants-1979_05
Patentnummer
US04153695

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