Methyl iodide → 5,7,N-trimethyl-N-(2,6-dichlorophenyl)-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonamide

HRID 477243Notes

Reaction equation

HRID 477243 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]2[N:9]=[C:10]([S:12]([NH:15][C:16]3[C:21]([Cl:22])=[CH:20][CH:19]=[CH:18][C:17]=3[Cl:23])(=[O:14])=[O:13])[N:11]=[C:4]2[N:3]=1.[CH3:24]C(C)([O-])C.[K+].CI>C(#N)C.C(Cl)Cl>[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]2[N:9]=[C:10]([S:12]([N:15]([CH3:24])[C:16]3[C:21]([Cl:22])=[CH:20][CH:19]=[CH:18][C:17]=3[Cl:23])(=[O:13])=[O:14])[N:11]=[C:4]2[N:3]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 179147Xrd 489HCID 23665647Potassium tert-butoxide

Product 1

HCID 141553575,7,N-trimethyl-N-(2,6-dichlorophenyl)-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonamideYield 51.4%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 3.00 g (8.06 mmol) of 5,7-dimethyl-N-(2,6-dichlorophenyl)-1,2,4-triazolo[1,5-a]-pyrimidine-2-sulfonamide and 0.90 g (8.1 mmol) of potassium t-butoxide in 30 ml of acetonitrile was heated at reflux for 40 minutes. After cooling to room temperature 1.14 g (8.06 mmol) of methyl iodide was added, and the reaction was heated at reflux for 1 hour. After cooling to room temperature, the reaction mixture was diluted with methylene chloride and washed with 1% aqueous NaOH. The organic phase was separated, dried (MgSO4) and evaporated at reduced pressure. The brown solid residue was recrystallized from acetone to give 1.60 g (51%) of the desire product as a tan solid, mp 220°-222° C. IR and 1H NMR spectra were in agreement with the assigned structure.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 40 minutes
  3. additionwas added
  4. temperaturethe reaction was heated
  5. temperatureat reflux for 1 hour
  6. washwashed with 1% aqueous NaOH
  7. customThe organic phase was separated
  8. dry with materialdried (MgSO4)
  9. customevaporated at reduced pressure
  10. customThe brown solid residue was recrystallized from acetone

Sources & evidence

ORD record
ord-304d8f1258e14feeb7209065d0ecf324
Source dataset
uspto-grants-1989_12
Patent number
US04886883

Reaction notes

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