Nicotinic Acid → N-[6-Imino-4-(4-methoxynaphthalen-1-yl)-1,6-dihydro-1,3,5-triazin-2-yl]pyridine-3-carboximidic acid

HRID 1981822Notes

Reaction equation

HRID 1981822 reaction equation
[C:1]([OH:9])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1.CS(Cl)(=O)=O.[NH2:15][C:16]1[N:21]=[C:20]([NH2:22])[N:19]=[C:18]([C:23]2[C:32]3[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=3)[C:26]([O:33][CH3:34])=[CH:25][CH:24]=2)[N:17]=1>N1C=CC=CC=1>[NH2:22][C:20]1[N:21]=[C:16]([NH:15][C:1](=[O:9])[C:2]2[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=2)[N:17]=[C:18]([C:23]2[C:32]3[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=3)[C:26]([O:33][CH3:34])=[CH:25][CH:24]=2)[N:19]=1

Participants

5

Reactant 3

HCID 938Nicotinic AcidHCID 31297Methanesulfonyl chloride2×HCID 119710996-(4-Methoxynaphthalen-1-yl)-1,3,5-triazine-2,4(1H,3H)-diimine

Product 1

HCID 11971097N-[6-Imino-4-(4-methoxynaphthalen-1-yl)-1,6-dihydro-1,3,5-triazin-2-yl]pyridine-3-carboximidic acid

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Nicotinic acid (2.98 grams) was dissolved in 40 ml of pyridine, 1.39 grams of methanesulfonyl chloride was added thereto, and the mixture was heated to reflux for thirty minutes. Then 2.7 grams of 2,4-diamino-6-(1-methoxy-4-naphthyl)-s-triazine was added thereto, the mixture was heated to reflux for four hours, and the refluxing was continued for three hours more after addition of 0.35 gram of methane sulfonyl chloride. After the reaction was completed, pyridine was evaporated therefrom, water was added to the residue, the crystals separated out were collected by filtration, well washed with water, added to 130 ml of methyl alcohol, the mixture was heated to reflux for twenty minutes, and the crystals were collected by filtration when the solution was still hot. The crystals were then suspended in 50 ml of methyl alcohol, the suspension was heated to reflux for three hours, and dioxane was added to the suspension to afford 2-amino-4-nicotinoylamino-6-(1-methoxy-4-naphthyl)-s-triazine, beige needles, melting point 208° to 209° C. The yield was 1.84 grams.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for thirty minutes
  3. temperaturethe mixture was heated
  4. temperatureto reflux for four hours
  5. custompyridine was evaporated
  6. additionwater was added to the residue
  7. customthe crystals separated out
  8. filtrationwere collected by filtration
  9. washwell washed with water
  10. additionadded to 130 ml of methyl alcohol
  11. temperaturethe mixture was heated
  12. temperatureto reflux for twenty minutes
  13. filtrationthe crystals were collected by filtration when the solution
  14. temperaturethe suspension was heated
  15. temperatureto reflux for three hours
  16. additiondioxane was added to the suspension

Sources & evidence

ORD record
ord-a0be0bffa296455bb658623d7cb00632
Source dataset
uspto-grants-1986_06
Patent number
US04593025

Reaction notes

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