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

HRID 1991318노트

반응식

HRID 1991318 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-b079846743a54d658a8462cc0c5495bd
출처 데이터셋
uspto-grants-2010_01
특허 번호
US07645781B2

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