Trifluoroacetic anhydride → 5-Chloro-3-(methoxycarbonyl)-2-methylpyrazine 1-oxide

HRID 627690노트

반응식

HRID 627690 반응식
[Cl:1][C:2]1[N:7]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[C:5]([CH3:12])=[N:4][CH:3]=1.C(N)(N)=[O:14].OO.FC(F)(F)C(OC(=O)C(F)(F)F)=O>ClCCl>[Cl:1][C:2]1[N:7]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[C:5]([CH3:12])=[N+:4]([O-:14])[CH:3]=1

참가 물질

5

반응물 3

HCID 9845Trifluoroacetic anhydrideHCID 31294Carbamide PeroxideHCID 57992035Methyl 6-chloro-3-methylpyrazine-2-carboxylate

생성물 1

HCID 867281445-Chloro-3-(methoxycarbonyl)-2-methylpyrazine 1-oxide수율 95%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To a solution of methyl 6-chloro-3-methylpyrazine-2-carboxylate (8.6 g, 46.1 mmol) and hydrogen peroxide urea adduct (8.1 g, 86 mmol) in dichloromethane (100 mL) was added 2,2,2-trifluoroacetic anhydride (10.9 ml, 78 mmol) dropwise. The resulting mixture was stirred at room temperature for 2 h. The reaction mixture was diluted with DCM and quenched with water. The aqueous layer was extracted with DCM. The combined organic extracts were dried (MgSO4), filtered and concentrated in vacuo to give the crude product 5-chloro-3-(methoxycarbonyl)-2-methylpyrazine 1-oxide (8.83 g, 43.6 mmol, 95% yield) which was used without further purification. 1H NMR (300 MHz, CDCl3) δ ppm 8.31 (1H, s), 4.02 (3H, s), 2.65 (3H, s).

후처리

  1. customquenched with water
  2. extractionThe aqueous layer was extracted with DCM
  3. dry with materialThe combined organic extracts were dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-744bd9f5361c4e71aefcf0cae120cc6f
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09309263B2

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