Triethylamine → 5-Methoxy-2-(methylamino)-4H-3,1-benzoxazin-4-one

HRID 598069

반응식

HRID 598069 반응식
[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH3:12])[C:3]=1[C:4]([OH:6])=[O:5].[CH3:13][N:14]=[C:15]=O.Cl.CN(C)CCCN=C=NCC.C(N(CC)CC)C>O1CCOCC1.O>[CH3:12][O:11][C:7]1[C:3]2[C:4](=[O:6])[O:5][C:13]([NH:14][CH3:15])=[N:1][C:2]=2[CH:10]=[CH:9][CH:8]=1

참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 12228Methyl IsocyanateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27353572-Amino-6-methoxybenzoic Acid

생성물 1

HCID 672673385-Methoxy-2-(methylamino)-4H-3,1-benzoxazin-4-one수율 43%

시약·촉매·용매 2

HCID 962Water용매HCID 312751,4-Dioxane용매

반응 조건

온도
80 °C

실험 절차

A mixture of 2-amino-6-methoxybenzoic acid (2.00 g, 12.0 mmol) and methylisocyanate (1.00 g, 17.5 mmol) in dioxane (50 ml) was stirred at 80° C. for 2 h. After cooling to room temperature, 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (6.88 g, 36.0 mmol) and triethylamine (5.00 ml, 36.0 mmol) were added. The mixture was stirred at room temperature for 16 h, diluted with water and extracted with ethyl acetate. The extract was washed with brine, dried over magnesium sulfate and concentrated under vacuum. The residue was purified by column chromatography eluting with 20% ethyl acetate/n-hexane to afford 1.06 g (43%) of the title compound.

후처리

  1. temperatureAfter cooling to room temperature
  2. stirringThe mixture was stirred at room temperature for 16 h
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under vacuum
  7. customThe residue was purified by column chromatography
  8. washeluting with 20% ethyl acetate/n-hexane

출처 및 근거

ORD 기록
ord-0c9d21e66dd648f997dd41525663635f
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07897607B2

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