Pyridine → 5,7-dimethyl-N-(2-acetoxymethyl-6-chlorophenyl)-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonamide

HRID 1251992Notes

Reaction equation

HRID 1251992 reaction equation
[C:1]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([Cl:12])[C:7]=1[NH2:13])(=[O:3])[CH3:2].N1C=CC=CC=1.[CH3:20][C:21]1[CH:26]=[C:25]([CH3:27])[N:24]2[N:28]=[C:29]([S:31](Cl)(=[O:33])=[O:32])[N:30]=[C:23]2[N:22]=1.S(Cl)(Cl)(=O)=O.[OH-].[Na+]>C(Cl)CCl.C(#N)C>[CH3:20][C:21]1[CH:26]=[C:25]([CH3:27])[N:24]2[N:28]=[C:29]([S:31]([NH:13][C:7]3[C:8]([Cl:12])=[CH:9][CH:10]=[CH:11][C:6]=3[CH2:5][O:4][C:1](=[O:3])[CH3:2])(=[O:32])=[O:33])[N:30]=[C:23]2[N:22]=1

Participants

8

Reactant 5

HCID 1049PyridineHCID 14798Sodium HydroxideHCID 24648Sulfuryl chlorideHCID 6112325,7-Dimethyl-[1,2,4]triazolo[1,5-a]pyrimidine-2-sulfonyl chlorideHCID 141554092-Acetoxymethyl-6-chloroaniline

Product 1

HCID 141552035,7-dimethyl-N-(2-acetoxymethyl-6-chlorophenyl)-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonamideYield 13.1%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
25 °C

Procedure

A solution of 1.30 gm (6.50 mmol) of 2-amino-3-chlorobenzyl acetate, 4.11 gm (52.0 mmol) of pyridine and 5.0 ml of acetonitrile was treated with 1.61 gm (6.50 mmol) of 5,7-dimethyl-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonyl chloride and the resulting mixture stirred at 25° C. for 120 hours. An additional 0.53 gm (2.2 mmol) of the sulfonyl chloride was added and stirring at 25° C. continued for an additional 24 hours. The mixture was filtered and the filtrate evaporated to provide a brown oil. The oil was then dissolved in 40 ml of m ethylene chloride and stirred with 25 ml of 0.5M NaOH. After 5 minutes, the aqueous phase was separated, washed with ether and acidified with 3N HCl. A light brown solid was collected, washed with water, dried and recrystallized from acetonitrile to provide 0.35 gm (13%) of the desired product as a solid, mp 214°-217° C., containing approximately 10% of an impurity. IR and 1H NMR spectra were in agreement with the assigned structure.

Workup

  1. stirringstirring at 25° C.
  2. waitcontinued for an additional 24 hours
  3. filtrationThe mixture was filtered
  4. customthe filtrate evaporated
  5. customto provide a brown oil
  6. waitAfter 5 minutes
  7. customthe aqueous phase was separated
  8. washwashed with ether
  9. customA light brown solid was collected
  10. washwashed with water
  11. customdried
  12. customrecrystallized from acetonitrile

Sources & evidence

ORD record
ord-964954f5cb5144889b3bd9c0262cbd37
Source dataset
uspto-grants-1988_05
Patent number
US04741764

Reaction notes

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