Toluene → 6-methoxy-2,4-dihydro-1H-3,1-benzoxazine-2,4-dione

HRID 635509

反応式

HRID 635509 の反応式
[CH3:1][O:2][C:3]1[CH:11]=[C:7]([C:8]([OH:10])=[O:9])[C:6]([NH2:12])=[CH:5][CH:4]=1.[C:13](Cl)(Cl)=[O:14].C(Cl)(Cl)=S.C1(C)C=CC=CC=1>O1CCOCC1>[CH3:1][O:2][C:3]1[CH:11]=[C:7]2[C:8]([O:10][C:13](=[O:14])[NH:12][C:6]2=[CH:5][CH:4]=1)=[O:9]

参加物

6

反応物 4

HCID 1140TolueneHCID 6371PhosgeneHCID 10040ThiophosgeneHCID 2779305-Methoxyanthranilic acid

生成物 1

HCID 2944796-methoxy-2,4-dihydro-1H-3,1-benzoxazine-2,4-dione収率 95.2%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

実験手順

To a mixture of 10.0 g (60.0 mmol) of 5-methoxyanthranilic acid in 80 mL of 1,4-dioxane was slowly added 100 mL (193 mmol) of a 1.93 molar solution of phosgene, or thiophosgene in an inert solvent, preferably a hydrocarbon solvent such as toluene, at room temperature. The mixture was stirred overnight at room temperature. This mixture was then concentrated in vacuo to a small volume. This concentrated reaction mixture was filtered through silica and the filter cake was washed with hexane to give 10.99 g (95.2%) of the 5-methoxyisatoic anhydride as an off white solid. MS (Cl mode) m/z 176 (M-18, 100%), 194 (M+H, 71%).

後処理

  1. customat room temperature
  2. concentrationThis mixture was then concentrated in vacuo to a small volume
  3. customThis concentrated reaction mixture
  4. filtrationwas filtered through silica
  5. washthe filter cake was washed with hexane

出典と根拠

ORDレコード
ord-9ce63da7e2df44f2baff914d599bd6d3
出典データセット
uspto-grants-2001_02
特許番号
US06187923B1

関連ノート

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