[(6-Fluoropyridin-2-yl)amino]urea → HCID 178433516, compound

HRID 1388786Notes

Reaction equation

HRID 1388786 reaction equation
[F:1][C:2]1[N:7]=[C:6]([NH:8][NH:9][C:10]([NH2:12])=[O:11])[CH:5]=[CH:4][CH:3]=1.[CH2:13](C(CC)(CC)C([O-])([O-])[O-])[CH3:14]>>[F:1][C:2]1[N:7]=[C:6]([N:8]2[C:13]([CH3:14])=[N:12][C:10]([OH:11])=[N:9]2)[CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 1478413[(6-Fluoropyridin-2-yl)amino]ureaHCID 21875354Triethylorthoaceate

Product 1

HCID 178433516HCID 178433516, compoundYield 58.7%

Procedure

A solution was prepared by admixing 17.02 g (0.10 m) of 2-(6-fluoro-2-pyridinyl)hydrazinecarboxamide with 100 ml of triethylorthoacetate. The mixture was refluxed overnight and the reaction mixture cooled to room temperature and poured over ice water. The solids which precipitated out were recovered by filtration. The solids were washed with methylene chloride and dried under vacuum to yield 11.4 g (58.7 percent of theoretical) of the desired 1-(6-fluoro-2-pyridinyl)-5-methyl-1H-1,2,4-triazol-3-ol. The product melted at 272°-274° C. and upon analysis was found to have carbon, hydrogen and nitrogen contents of 49.58, 3.83 and 28.88 percent, respectively, as compared with the theoretical contents of 49.48, 3.63 and 28.85 percent, respectively, as calculated for the above named compound.

Workup

  1. customA solution was prepared
  2. temperatureThe mixture was refluxed overnight
  3. customThe solids which precipitated out
  4. filtrationwere recovered by filtration
  5. washThe solids were washed with methylene chloride
  6. customdried under vacuum

Sources & evidence

ORD record
ord-a6d8249dfb0b4ed28da3b38056bfe9b4
Source dataset
uspto-grants-1984_02
Patent number
US04433148

Reaction notes

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