Urea → Isonicotinoyl Urea

HRID 261018

Reaction equation

HRID 261018 reaction equation
[NH2:1][C:2]([NH2:4])=[O:3].[Na].[C:6](OC)(=[O:13])[C:7]1[CH:12]=[CH:11][N:10]=[CH:9][CH:8]=1>N>[C:6]([NH:1][C:2]([NH2:4])=[O:3])(=[O:13])[C:7]1[CH:12]=[CH:11][N:10]=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 1176UreaHCID 227085Methyl isonicotinateHCID 5360545Sodium

Product 1

HCID 13851072Isonicotinoyl Urea

Reagents, catalysts & solvents 1

HCID 222AmmoniaSolvent2×

Procedure

Urea (7.5 g., 0.125 mole) is suspended in liquid ammonia (250 ml.) in a round bottom flask fitted with an acetone/dry-ice condenser. Sodium pellets (2.9 g., 0.125 mole) are added and, after they have dissolved, methyl isonicotinate (12 g., 0.089 mole) is added to the mixture. The ammonia is allowed to evaporate from the mixture overnight. The yellow-tan residue is dissolved in water (150 ml.), the pH of the mixture adjusted to 5.5 with glacial acetic acid, and the precipitate which forms filtered, washed with water and air dired. It is then washed with hexane and triturated with boiling methanol. The white solid (isonicotinic acid) is removed by filtration and the filtrate evaporated to dryness to give the title product as a yellowish solid: m.p. 245°-247° C. Quantitative analysis and infra-red data are consistent with the values expected for the product.

Workup

  1. customfitted with an acetone/dry-ice condenser
  2. dissolutionafter they have dissolved
  3. customto evaporate from the mixture overnight
  4. dissolutionThe yellow-tan residue is dissolved in water (150 ml.)
  5. filtrationthe precipitate which forms filtered
  6. washwashed with water and air dired
  7. washIt is then washed with hexane
  8. customtriturated with boiling methanol
  9. customThe white solid (isonicotinic acid) is removed by filtration
  10. customthe filtrate evaporated to dryness

Sources & evidence

ORD record
ord-cc914c8bf1fe40c3a16015a85b2efecd
Source dataset
uspto-grants-1979_08
Patent number
US04163784

Linked notes

Loading…