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

HRID 896182노트

반응식

HRID 896182 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+].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

5

반응물 3

HCID 962WaterHCID 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 Mel (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. additionfollowed by addition of Mel (0.87 mL, 14.07 mmol)
  2. extractionthe resulting solution is extracted with EtOAc (50 mL×3)
  3. washThe combined organic phases are washed with water (50 mL) and saline (50 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-fe24220c7bf24b6f87a3dba62c3200c0
출처 데이터셋
uspto-grants-2005_07
특허 번호
US06919329B2

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