Water → 2,2-difluoro-4-methyl-7-nitro-4H-1,4-benzoxazin-3-one

HRID 1991318ノート

反応式

HRID 1991318 の反応式
[F:1][C:2]1([F:16])[C:7](=[O:8])[NH:6][C:5]2[CH:9]=[CH:10][C:11]([N+:13]([O-:15])=[O:14])=[CH:12][C:4]=2[O:3]1.[C:17]([O-])([O-])=O.[K+].[K+].CI.O>CN(C=O)C>[F:16][C:2]1([F:1])[C:7](=[O:8])[N:6]([CH3:17])[C:5]2[CH:9]=[CH:10][C:11]([N+:13]([O-:15])=[O:14])=[CH:12][C:4]=2[O:3]1

参加物

6

反応物 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 218781552,2-difluoro-7-nitro-4H-1,4-benzoxazin-3-one

生成物 1

HCID 218781062,2-difluoro-4-methyl-7-nitro-4H-1,4-benzoxazin-3-one

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a stirred suspension of 2,2-difluoro-7-nitro-4H-1,4-benzoxazin-3-one (WO 99/40094, 2.16 g, 9.38 mmol) in DMF (10 mL) is added K2CO3 (1.94 g, 14.07 mmol) followed by addition of MeI (0.87 mL, 14.07 mmol). The resulting solution is stirred over night at room temperature. To this reaction mixture is added water (50 mL), and the resulting solution is extracted with EtOAc (50 mL×3). The combined organic phases are washed with water (50 mL) and saline (50 mL), dried over Na2SO4 and concentrated under reduced pressure to give the title compound that is purified by passing through a short silica gel column with EtOAc (1.3 g, 57%), 1H NMR (300 MHz, DMSO) δ 8.25-8.17 (m, 2H), 7.62 (d, 1H), 3.47 (s, 3H).

後処理

  1. extractionthe resulting solution is extracted with EtOAc (50 mL×3)
  2. washThe combined organic phases are washed with water (50 mL) and saline (50 mL)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-b079846743a54d658a8462cc0c5495bd
出典データセット
uspto-grants-2010_01
特許番号
US07645781B2

反応ノート

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