Propargyl bromide → 2H-1,4-benzoxazin-3(4H)-one

HRID 1735072노트

반응식

HRID 1735072 반응식
ClC1C([C:12]2[C:13](F)=[CH:14][C:15]3[O:20][CH2:19][C:18](=[O:21])[NH:17][C:16]=3[CH:22]=2)=NN(C)C=1C(F)(F)F.C([O-])([O-])=O.[K+].[K+].C(Br)C#C>CC(C)=O.O>[O:20]1[C:15]2[CH:14]=[CH:13][CH:12]=[CH:22][C:16]=2[NH:17][C:18](=[O:21])[CH2:19]1

참가 물질

6

반응물 3

HCID 7842Propargyl bromideHCID 11430Potassium CarbonateHCID 194367686-(4-chloro-1-methyl-5-(trifluoromethyl)-1H-pyrazol-3-yl)-7-fluoro-2H-1,4-benzoxazin-3(4H)-one

생성물 1

HCID 727572H-1,4-benzoxazin-3(4H)-one수율 231.5%

시약·촉매·용매 2

HCID 180Acetone용매HCID 962Water용매

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온도
40 °C

실험 절차

At 25° C., 3.0 g (8.6 mmole) of the product of step A, 1.22 g (6.0 mmole) K2CO3 and 0.79 mL (8.8 mmole) 80% propargyl bromide were slurried in 50 mL acetone. The reaction was stirred at 40° C. for 6 hours. The reaction was cooled, diluted with 100 mL cold water, and extracted four times with ethyl acetate. The ethyl acetate extracts were washed with brine, dried over anhydrous MgSO4, and stripped in vacuo. The residue was recrystallized from methylcyclohexane to give 2.97 g (89%) of 2H-1,4-benzoxazin-3(4H)-one, 6-(4-chloro-1-methyl-5-(trifluoromethyl)-1H-pyrazol-3-yl)-7-fluoro-4(2-propynyl)-2H-1,4-benzoxazin-3(4H)-one as a beige solid, mp 142°-143° C.

후처리

  1. customAt 25° C.
  2. temperatureThe reaction was cooled
  3. extractionextracted four times with ethyl acetate
  4. washThe ethyl acetate extracts were washed with brine
  5. dry with materialdried over anhydrous MgSO4
  6. customThe residue was recrystallized from methylcyclohexane

출처 및 근거

ORD 기록
ord-5b4d37af378d44e2bf9ec3740192aa87
출처 데이터셋
uspto-grants-1996_07
특허 번호
US05536700

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