Sodium Methoxide → HCID 13137351, compound

HRID 1248313Notes

Reaction equation

HRID 1248313 reaction equation
[CH:1]([CH:3]([CH2:9][C:10]1[O:11][CH:12]=[CH:13][CH:14]=1)[C:4](OCC)=O)=[O:2].[N+:15]([NH:18][C:19]([NH2:21])=[NH:20])([O-:17])=[O:16].C[O-].[Na+]>CO>[N+:15]([NH:18][C:19]1[NH:21][C:1](=[O:2])[C:3]([CH2:9][C:10]2[O:11][CH:12]=[CH:13][CH:14]=2)=[CH:4][N:20]=1)([O-:17])=[O:16]

Participants

5

Reactant 3

HCID 10942334Sodium MethoxideHCID 20279269HCID 20279269, compoundHCID 86287517Nitroguanidine

Product 1

HCID 13137351HCID 13137351, compoundYield 59.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Ethyl 2-formyl-3-(2-furyl)propionate (24.0 g, 0.122 mol) was added to a mixture of nitroguanidine (12.69 g, 0.122 mol) and sodium methoxide (from 3.09 g, 0.134 mol, sodium) in methanol and the mixture was stirred and heated under reflux for 18 hours and evaporated to dryness. The residue was dissolved in water and the solution was adjusted to pH 4 with acetic acid. The solid which separated was filtered off to give 2-nitroamino-5-(2-furylmethyl)-4-pyrimidone (17.1 g, 59%). A sample recrystallized from methanol-acetic acid and from acetic acid had m.p. 183°-184°.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 18 hours
  3. customevaporated to dryness
  4. dissolutionThe residue was dissolved in water
  5. customThe solid which separated
  6. filtrationwas filtered off

Sources & evidence

ORD record
ord-df3accba184a44878374ce76adafa828
Source dataset
uspto-grants-1985_06
Patent number
US04523015

Reaction notes

Loading…