Dimethylformamide → 6,6-Difluoro-5-methyl-5-hexenyl 6-aminonicotinate

HRID 917359

반응식

HRID 917359 반응식
CN(C)C=O.CS([O:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]([CH3:19])=[C:16]([F:18])[F:17])(=O)=O.[NH2:20][C:21]1[CH:29]=[CH:28][C:24]([C:25](O)=[O:26])=[CH:23][N:22]=1.C(=O)([O-])O.[Na+]>O>[NH2:20][C:21]1[CH:29]=[CH:28][C:24]([C:25]([O:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]([CH3:19])=[C:16]([F:18])[F:17])=[O:26])=[CH:23][N:22]=1

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 184966-Aminonicotinic acidHCID 516892Sodium BicarbonateHCID 230203716,6-Difluoro-5-methyl-5-hexenyl methanesulfonate

생성물 1

HCID 230203546,6-Difluoro-5-methyl-5-hexenyl 6-aminonicotinate수율 78.6%

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
100 °C

실험 절차

To 7 ml of N,N-dimethylformamide were dissolved 0.92 g (4.0 mmol) of 6,6-difluoro-5-methyl-5-hexenyl methanesulfonate and 0.72 g (5.2 mmol) of 6-aminonicotinic acid, followed by the addition of 1.30 g (16 mmol) of sodium hydrogencarbonate and stirring at 100° C. for 3 hours. The reaction liquid was then poured in water and extracted with ethyl acetate. The organic layer was washed with water and a saturated saline solution in this order, followed by drying over anhydrous magnesium sulfate and concentration under reduced pressure. The residue was purified with silica gel column chromatography (ethyl acetate:hexane=1:1) to obtain 0.85 g (yield: 78%) of 6,6-difluoro-5-methyl-5-hexenyl 6-aminonicotinate.

후처리

  1. customThe reaction liquid
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materialby drying over anhydrous magnesium sulfate and concentration under reduced pressure
  5. customThe residue was purified with silica gel column chromatography (ethyl acetate:hexane=1:1)

출처 및 근거

ORD 기록
ord-d887f99e52204fbf8dc28b0181e8ef2c
출처 데이터셋
uspto-grants-2007_09
특허 번호
US07273878B2

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