tert-Butylhydrazine monohydrochloride → 2-Tert-butyl-4,5-dichloro-2,3-dihydropyridazin-3-one

HRID 381922

반응식

HRID 381922 반응식
[C:1](O)(=O)/[C:2](=[C:4](\[CH:6]=[O:7])/[Cl:5])/[Cl:3].Cl.[C:11]([NH:15][NH2:16])([CH3:14])([CH3:13])[CH3:12]>CO>[C:11]([N:15]1[C:6](=[O:7])[C:4]([Cl:5])=[C:2]([Cl:3])[CH:1]=[N:16]1)([CH3:14])([CH3:13])[CH3:12]

참가 물질

4

반응물 2

HCID 81889tert-Butylhydrazine monohydrochlorideHCID 2771871Mucochloric Acid

생성물 1

HCID 27822252-Tert-butyl-4,5-dichloro-2,3-dihydropyridazin-3-one

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

A solution of mucochloric acid (33.8 g, 200 mmol) and tert.-butylhydrazine hydrochloride (24.9 g, 200 mmol) in methanol (400 mL) was stirred at reflux overnight. Methanol was removed in vacuo and the residue was partitioned between ether and water. The organic layer was dried over MgSO4 and filtered. The filtrate was concentrated in vacuo and the residue was purified by column chromatography (silica gel, 100% hexanes). Product-containing fractions were combined and the title compound was crystallized from ether/hexanes (yield: 10.0 g, 22.6%). mp 63-64° C. 1H NMR (300 MHz, CDCl3) δ 1.65 (s, 9H), 7.73 (s, 1H). MS (DCI/NH3) m/z 221 (M+H)+, 238 (M+NH4)+.

후처리

  1. temperatureat reflux overnight
  2. customMethanol was removed in vacuo
  3. customthe residue was partitioned between ether and water
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated in vacuo
  7. customthe residue was purified by column chromatography (silica gel, 100% hexanes)
  8. customthe title compound was crystallized from ether/hexanes (yield: 10.0 g, 22.6%)

출처 및 근거

ORD 기록
ord-897d36f9f0804f8eb20208ec60bbddc0
출처 데이터셋
uspto-grants-2001_10
특허 번호
US06307047B1

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