Dimethylformamide → 4-(2-methoxy-4-(trifluoromethyl)phenyl)-7-nitro-2H-benzo[b][1,4]oxazin-3(4H)-one

HRID 528638노트

반응식

HRID 528638 반응식
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:6]=[CH:5][C:4]=1[NH:13][C:14]1[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][C:15]=1[OH:23].C(=O)([O-])[O-].[Cs+].[Cs+].CN(C=O)C.Cl[CH2:36][C:37](Cl)=[O:38]>CCOC(C)=O>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:6]=[CH:5][C:4]=1[N:13]1[C:37](=[O:38])[CH2:36][O:23][C:15]2[CH:16]=[C:17]([N+:20]([O-:22])=[O:21])[CH:18]=[CH:19][C:14]1=2

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 6577Chloroacetyl chlorideHCID 10796Cesium carbonateHCID 897612612-((2-Methoxy-4-(trifluoromethyl)phenyl)amino)-5-nitrophenol

생성물 1

HCID 897619994-(2-methoxy-4-(trifluoromethyl)phenyl)-7-nitro-2H-benzo[b][1,4]oxazin-3(4H)-one수율 107%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

To a flask charged with 2-((2-methoxy-4-(trifluoromethyl)phenyl)amino)-5-nitrophenol (1.75 g, 5.33 mmol) and cesium carbonate (8.69 g, 26.7 mmol) was added DMF (21.33 ml) followed by chloroacetyl chloride (0.854 ml, 10.66 mmol), dropwise over 5 min. The resulting solution was maintained at rt for 1 h. Quenched reaction with saturated ammonium chloride (25 mL) and diluted with EtOAc (25 mL). Separated layers, and extracted aqueous layer with EtOAc (3×25 mL). The combined organic layers were dried over Na2SO4, filtered, and concentrated via rotary evaporation to provide 4-(2-methoxy-4-(trifluoromethyl)phenyl)-7-nitro-2H-benzo[b][1,4]oxazin-3(4H)-one (2.10 g, 5.70 mmol, 107% yield) as a yellow solid. The crude product was used in the next step without further purification.

후처리

  1. customQuenched
  2. customreaction with saturated ammonium chloride (25 mL)
  3. extractionSeparated layers, and extracted aqueous layer with EtOAc (3×25 mL)
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated via rotary evaporation

출처 및 근거

ORD 기록
ord-56506c9d8ad346ddb675c3f937d435a2
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09346798B2

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