Water → HCID 178456876, compound

HRID 1580588Notes

Reaction equation

HRID 1580588 reaction equation
[NH2:1][C:2]1[N:7]=[C:6](Cl)[C:5]([N+:9]([O-:11])=[O:10])=[C:4]([OH:12])[N:3]=1.Cl.[NH2:14][C:15]([CH3:28])([CH3:27])[C:16](=[N:25][OH:26])[CH2:17][O:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(N(CC)CC)C.O>C(O)C>[NH2:1][C:2]1[N:3]=[C:4]([OH:12])[C:5]([N+:9]([O-:11])=[O:10])=[C:6]([NH:14][C:15]([CH3:28])([CH3:27])[C:16](=[N:25][OH:26])[CH2:17][O:18][C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[N:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 867329813-Amino-1-phenoxy-3-methylbutan-2-one oxime hydrochlorideHCID 178418667HCID 178418667, compound

Product 1

HCID 178456876HCID 178456876, compoundYield 48.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-amino-4-chloro-6-hydroxy-5-nitropyrimidine (III) (Hal = Cl) (1.53 g), 3-amino-1-(p-methoxy)phenoxy-3-methylbutan-2-one oxime hydrochloride (IV) (2.2 g) and dry triethylamine (1.70 g) in dry ethanol (20 ml) was refluxed for 2 hours. The mixture was cooled, water (50 ml) was added, and the resulting precipitate was filtered off and dried. Recrystallisation from a mixture of water and ethanol gave the nitropyrimidine oxime (II) (1.4 g, yield 48%) as pale yellow crystals, m.p. 242° (decomp.).

Workup

  1. temperaturewas refluxed for 2 hours
  2. temperatureThe mixture was cooled
  3. filtrationthe resulting precipitate was filtered off
  4. customdried
  5. customRecrystallisation
  6. additionfrom a mixture of water and ethanol

Sources & evidence

ORD record
ord-3264b355aebc4df8a20c44052a0db5ae
Source dataset
uspto-grants-1976_01
Patent number
US03933820

Reaction notes

Loading…