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

HRID 1031369노트

반응식

HRID 1031369 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 6342Acetonitrile용매HCID 6344Dichloromethane용매

실험 절차

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%) the desire product as a tan solid, mp 220°-222° C. IR and 1H NMR spectra were in agreement with the assigned structure.

후처리

  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

출처 및 근거

ORD 기록
ord-c741534aaee64b8cbddfbfe6e1940d5a
출처 데이터셋
uspto-grants-1990_09
특허 번호
US04954163

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