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1,1-Dimethylhydrazine → 3-(5-Methyl-3-phenyl-isoxazol-4-ylmethoxy)-isoxazole-5-carboxylic acid N',N'-dimethyl-hydrazide

HRID 1920901
ノート
印刷プレビュー

反応式

HRID 1920901 の反応式
C[Al](C)C.[CH3:5][N:6]([CH3:8])[NH2:7].C[O:10][C:11]([C:13]1[O:17][N:16]=[C:15]([O:18][CH2:19][C:20]2[C:21]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[N:22][O:23][C:24]=2[CH3:25])[CH:14]=1)=O.[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+]>O1CCOCC1>[CH3:5][N:6]([CH3:8])[NH:7][C:11]([C:13]1[O:17][N:16]=[C:15]([O:18][CH2:19][C:20]2[C:21]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[N:22][O:23][C:24]=2[CH3:25])[CH:14]=1)=[O:10]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 59761,1-DimethylhydrazineHCID 9357Potassium Sodium TartrateHCID 16682925TrimethylaluminumHCID 674922963-(5-Methyl-3-phenyl-isoxazol-4-ylmethoxy)-isoxazole-5-carboxylic acid methyl ester

生成物 1

HCID 468974553-(5-Methyl-3-phenyl-isoxazol-4-ylmethoxy)-isoxazole-5-carboxylic acid N',N'-dimethyl-hydrazide収率 22%

試薬・触媒・溶媒

1
HCID 312751,4-Dioxane溶媒

実験手順

A solution of trimethylaluminium (2 M in toluene, 0.6 mL, 1.3 mmol) was added dropwise (exothermic) to a solution of N,N-dimethylhydrazine (76 mg, 1.3 mmol) in dioxane (5 mL) and the resulting mixture was stirred at room temperature for 1 h. Then 3-(5-methyl-3-phenyl-isoxazol-4-ylmethoxy)-isoxazole-5-carboxylic acid methyl ester (100 mg, 0.32 mmol) was added. The resulting mixture was then heated at 85-90° C. for 4 h and then cooled to room temperature and then poured into Seignette's salt and extracted with ethyl acetate which was then washed with brine, dried over sodium sulfate and evaporated. Purification by chromatography (silica, dichloromethane:methanol=9:1 to 4:1) afforded the title compound (24 mg, 22%) which was obtained as a colourless oil. MS: m/e=343.3 [M+H]+.

後処理

  1. temperatureThe resulting mixture was then heated at 85-90° C. for 4 h
  2. temperaturecooled to room temperature
  3. extractionextracted with ethyl acetate which
  4. washwas then washed with brine
  5. dry with materialdried over sodium sulfate
  6. customevaporated
  7. customPurification by chromatography (silica, dichloromethane:methanol=9:1 to 4:1)

出典と根拠

ORDレコード
ord-1687ed7e22c14d04b1541d8a7b8c63ad
出典データセット
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08173652B2

反応ノート

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