Acetone → 2,2-dimethyl-3,4-dihydro-2H-1,3-benzoxazin-4-one

HRID 381254

反応式

HRID 381254 の反応式
[C:1]([NH2:10])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4].[CH3:11][C:12]([CH3:14])=O>S(=O)(=O)(O)O>[CH3:11][C:12]1([CH3:14])[NH:10][C:1](=[O:9])[C:2]2[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=2[O:4]1

参加物

4

反応物 2

HCID 180AcetoneHCID 5147Salicylamide

生成物 1

HCID 7174282,2-dimethyl-3,4-dihydro-2H-1,3-benzoxazin-4-one収率 47%

試薬・触媒・溶媒 1

HCID 1118Sulfuric Acid触媒

実験手順

A solution of salicylamide (4.14 g, 30.2 mmol) and conc. sulfuric acid (3 drops) in acetone (40 mL) was refluxed for 5 h. The reaction was concentrated and the residue taken up in ethyl acetate. The organic solution was washed with 1 N NaOH (2×), 1 N HCl (2×), H2O, then sat. aq. NaCl, dried (MgSO4) and concentrated to afford 2,2-dimethyl-4-keto-1,3-benzoxazine (2.50 g, 47%) as a white solid: 1H NMR (CDCl3, 300 MHz, ppm) 7.92 (d, 1H), 7.60 (bs, 1H), 7.47 (m, 1H), 7.06 (m, 1H), 6.92 (d, 1H), 1.65 (s, 6H).

後処理

  1. concentrationThe reaction was concentrated
  2. washThe organic solution was washed with 1 N NaOH (2×), 1 N HCl (2×), H2O
  3. dry with materialsat. aq. NaCl, dried (MgSO4)
  4. concentrationconcentrated

出典と根拠

ORDレコード
ord-b9c42934fda945d39d4fe458fd9a2870
出典データセット
uspto-grants-2001_10
特許番号
US06306840B1

関連ノート

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