Sodium Methoxide → HCID 13137351, compound

HRID 903367Notes

Reaction equation

HRID 903367 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 recrystallised 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-9e06374e2233453cb439318cfec01f37
Source dataset
uspto-grants-1980_10
Patent number
US04227000

Reaction notes

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