Acetic Acid → 5-Methyl-2-(4-nitrophenyl)oxazole

HRID 880489ノート

反応式

HRID 880489 の反応式
[N+:1]([C:4]1[CH:15]=[CH:14][C:7]([C:8]([NH:10][CH2:11][C:12]#[CH:13])=[O:9])=[CH:6][CH:5]=1)([O-:3])=[O:2].[OH-].[K+].C(O)(=O)C>C(O)C>[CH3:13][C:12]1[O:9][C:8]([C:7]2[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:15][CH:14]=2)=[N:10][CH:11]=1

参加物

5

反応物 3

HCID 176Acetic AcidHCID 14797Potassium HydroxideHCID 3016782Benzamide, 4-nitro-N-2-propynyl-

生成物 1

HCID 445506455-Methyl-2-(4-nitrophenyl)oxazole収率 46.3%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒2 回

反応条件

温度
52.5 °C

実験手順

To a stirred solution of 4-nitro-N-prop-2-ynyl-benzamide (7.5 g, 36.7 mmol) in ethanol (150 mL) was added a solution of potassium hydroxide (4.1 g, 73.4 mmol) in ethanol (100 mL) and the mixture was stirred at 50-55° C. for 12 h. The mixture was acidified with acetic acid and concentrated to dryness in vacuo at 45-50° C. The resultant residue was extracted into ethyl acetate and the separated organic phase was washed with water; aqueous sodium bicarbonate, brine, dried over anhydrous sodium sulphate and concentrated in vacuo to afford 5-methyl-2-(4-nitrophenyl)oxazole (3.47 g, 46%) as an oil.

後処理

  1. concentrationconcentrated to dryness in vacuo at 45-50° C
  2. extractionThe resultant residue was extracted into ethyl acetate
  3. washthe separated organic phase was washed with water
  4. dry with materialaqueous sodium bicarbonate, brine, dried over anhydrous sodium sulphate
  5. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-5f22c9d01cbe4ef58247bbea52653ef0
出典データセット
uspto-grants-2015_03
特許番号
US08993574B2

反応ノート

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