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

HRID 262118

Reaction equation

HRID 262118 reaction equation
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]

Participants

8

Reactant 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

Product 1

HCID 178526808HCID 178526808, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6212ChloroformSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-a6cb9de849fe45bd9d458bc5c047d3d7
Source dataset
uspto-grants-1979_05
Patent number
US04153695

Linked notes

Loading…