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

HRID 381254

반응식

HRID 381254 반응식
[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

참가 물질

4

반응물 2

HCID 180AcetoneHCID 5147Salicylamide

생성물 1

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

시약·촉매·용매 1

HCID 1118Sulfuric Acid촉매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-b9c42934fda945d39d4fe458fd9a2870
출처 데이터셋
uspto-grants-2001_10
특허 번호
US06306840B1

연결된 노트

불러오는 중…