Sulfuric Acid → 3,6-Dichloro-4-cyclobutylpyridazine

HRID 380321

반응식

HRID 380321 반응식
[Cl:1][C:2]1[N:3]=[N:4][C:5]([Cl:8])=[CH:6][CH:7]=1.OS(O)(=O)=O.[CH:14]1(C(O)=O)[CH2:17][CH2:16][CH2:15]1>O>[Cl:1][C:2]1[N:3]=[N:4][C:5]([Cl:8])=[CH:6][C:7]=1[CH:14]1[CH2:17][CH2:16][CH2:15]1

참가 물질

5

반응물 3

HCID 1118Sulfuric AcidHCID 19494Cyclobutanecarboxylic acidHCID 673313,6-Dichloropyridazine

생성물 1

HCID 219732193,6-Dichloro-4-cyclobutylpyridazine수율 98.3%

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
70 °C

실험 절차

3,6-Dichloropyridazine (10 g) was suspended in water (200 ml), H2SO4 (19.7 g) and cyclobutane carboxylic acid (32.7 g) were added and the reaction degassed under N2 at 70° C. Silver nitrate (2.28 g) was added followed by dropwise addition of ammonium persulfate (45.9 g) in water (120 ml). After an additional 1 hour heating at 70° C., the reaction was poured onto ice, basified to pH 8-9 with aqueous ammonium hydroxide and extracted into ethyl acetate (3×500 ml), dried (MgSO4) and evaporated to dryness. Purified with hexane-ethyl acetate mixtures to obtain pure product (13.4 g). 1H NMR (360 MHz , CDCl3) δ 1.57 (2H, m), 1.82 (4H, m), 2.20 (1H, m), 3.30 (1H, m), 7.38 (1H, s); MS (ES+) m/e 217 [MH]+.

후처리

  1. customthe reaction degassed under N2 at 70° C
  2. additionSilver nitrate (2.28 g) was added
  3. additionfollowed by dropwise addition of ammonium persulfate (45.9 g) in water (120 ml)
  4. additionthe reaction was poured onto ice
  5. extractionextracted into ethyl acetate (3×500 ml)
  6. dry with materialdried (MgSO4)
  7. customevaporated to dryness
  8. customPurified with hexane-ethyl acetate mixtures

출처 및 근거

ORD 기록
ord-3671f2e139124d1da48098d0c6ba8df0
출처 데이터셋
uspto-grants-2001_10
특허 번호
US06303605B1

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