2-Thenoylacetonitrile → 3-(2-Thienyl)-5-isoxazolamine

HRID 595043

反応式

HRID 595043 の反応式
[C:1]1([C:6]([CH2:8][C:9]#[N:10])=O)[S:5][CH:4]=[CH:3][CH:2]=1.Cl.[NH2:12][OH:13].C([O-])(=O)C.[Na+]>C(Cl)Cl.CO>[S:5]1[CH:4]=[CH:3][CH:2]=[C:1]1[C:6]1[CH:8]=[C:9]([NH2:10])[O:13][N:12]=1

参加物

6

反応物 3

HCID 1418532-ThenoylacetonitrileHCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium Acetate

生成物 1

HCID 2169013-(2-Thienyl)-5-isoxazolamine

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
40 °C

実験手順

A mixture of 2-thenoylacetonitrile (1 g, 6.6 mmol), hydroxylamine hydrochloride (1.38 g, 19.8 mmol) and sodium acetate (2.17 g, 26.5 mmol) in DCM (20 ml) and MeOH (20 ml) was heated at 40° C. overnight, cooled to rt and concentrated. The residue was partitioned between EtOAc and water, the organic layer was washed with water, brine, dried over magnesium sulfate and concentrated to give a brown solid 1-4. 1H NMR (400 MHz, CDCl3) δ 7.38 (m, 2H), 7.08 (m, 1H), 5.40 (s, 1H), 4.49 (bs, 21-1); ESI+ MS [M+H]+ C7H7N2OS=167.1.

後処理

  1. temperaturecooled to rt
  2. concentrationconcentrated
  3. customThe residue was partitioned between EtOAc and water
  4. washthe organic layer was washed with water, brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-2ea3c3eee1d74e1a8557b8d98a565e31
出典データセット
uspto-grants-2016_01
特許番号
US09242995B2

関連ノート

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