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

HRID 381922ノート

反応式

HRID 381922 の反応式
[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]

参加物

4

反応物 2

HCID 81889tert-Butylhydrazine monohydrochlorideHCID 2771871Mucochloric Acid

生成物 1

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

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

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)+.

後処理

  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%)

出典と根拠

ORDレコード
ord-897d36f9f0804f8eb20208ec60bbddc0
出典データセット
uspto-grants-2001_10
特許番号
US06307047B1

反応ノート

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