Diisopropylethylamine → 1-ethyl-5-(2-methyl-propenyl)-3-pyrrolidin-1-yl-1H-[1,2,4]triazole

HRID 1054924ノート

反応式

HRID 1054924 の反応式
[CH3:1][C:2]([CH3:15])=[CH:3][C:4](/[N:6]=[C:7](/[N:10]1[CH2:14][CH2:13][CH2:12][CH2:11]1)\SC)=O.C(O)(=O)C(O)=O.[CH2:22]([NH:24][NH2:25])[CH3:23].C(N(CC)C(C)C)(C)C>O1CCOCC1.C(OCC)(=O)C>[CH2:22]([N:24]1[C:4]([CH:3]=[C:2]([CH3:15])[CH3:1])=[N:6][C:7]([N:10]2[CH2:14][CH2:13][CH2:12][CH2:11]2)=[N:25]1)[CH3:23]

参加物

6

反応物 3

HCID 81531DiisopropylethylamineHCID 96181Hydrazine, ethyl-, ethanedioate (1:1)HCID 178503950HCID 178503950、化合物

生成物 1

HCID 900179801-ethyl-5-(2-methyl-propenyl)-3-pyrrolidin-1-yl-1H-[1,2,4]triazole収率 38.1%

試薬・触媒・溶媒 2

HCID 8857Ethyl Acetate溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
100 °C

実験手順

A mixture of (Z)-methyl N-3-methylbut-2-enoylpyrrolidine-1-carbimidothioate (1.19 g, 5.26 mmol, Eq: 1.00), ethylhydrazine oxalate (2.37 g, 15.8 mmol, Eq: 3) and N,N-diisopropyl ethyl amine (5.44 g, 7.15 ml, 42.1 mmol, Eq: 8) in dioxane (20 ml) was heated to 100° C., the resulting suspension was stirred for 3 hours at 100° C. The mixture was diluted with ethyl acetate and washed with water for 3 times. The organic layer was separated, dried over magnesium sulfate, filtrated and evaporated. The crude material was applied on silicagel and purified by flash chromatography over a 20 g silicagel column using heptane/ethyl acetate 30-70% as eluent affording 1-ethyl-5-(2-methyl-propenyl)-3-pyrrolidin-1-yl-1H-[1,2,4]triazole (441 mg/38.1%) as a light yellow oil. MS: m/e=221.0 (M+H+)

後処理

  1. washwashed with water for 3 times
  2. customThe organic layer was separated
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltrated
  5. customevaporated
  6. custompurified by flash chromatography over a 20 g silicagel column

出典と根拠

ORDレコード
ord-a49f76652f9e4e86bb0b2a5ee6e41b9e
出典データセット
uspto-grants-2016_07
特許番号
US09394311B2

反応ノート

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