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

HRID 598069

反応式

HRID 598069 の反応式
[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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
80 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-0c9d21e66dd648f997dd41525663635f
出典データセット
uspto-grants-2011_03
特許番号
US07897607B2

関連ノート

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