Water → Flupyradifurone

HRID 1037639

반응식

HRID 1037639 반응식
O.[Cl:2][C:3]1[N:8]=[CH:7][C:6]([CH2:9][NH:10][CH2:11][CH:12]([F:14])[F:13])=[CH:5][CH:4]=1.[CH2:15]1[C:20](=[O:21])[O:19][CH2:18][C:16]1=O>C1(C)C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>[Cl:2][C:3]1[N:8]=[CH:7][C:6]([CH2:9][N:10]([CH2:11][CH:12]([F:14])[F:13])[C:16]2[CH2:18][O:19][C:20](=[O:21])[CH:15]=2)=[CH:5][CH:4]=1

참가 물질

6

반응물 3

HCID 962WaterHCID 521261Tetronic acidHCID 44604123N-[(6-chloropyridin-3-yl)methyl]-2,2-difluoroethanamine

생성물 1

HCID 16752772Flupyradifurone수율 52%

시약·촉매·용매 2

HCID 6101p-Toluenesulfonic acid촉매HCID 1140Toluene용매

실험 절차

On a water separator, 21.90 g (106.0 mmol) of N-[(6-chloropyridin-3-yl)methyl]-2,2-difluoroethane-1-amine (III-1), 14.85 g (148.4 mmol) of tetronic acid and 183 mg (1.1 mmol) of 4-toluenesulphonic acid in 250 ml of toluene are heated under reflux for 2 hours. The reaction mixture is concentrated under reduced pressure, the residue is then taken up in ethyl acetate and the mixture is washed successively twice with 1 N aqueous hydrochloric acid, twice with 1 N aqueous sodium hydroxide solution and once with saturated sodium chloride solution. The organic phase is dried over sodium sulphate and concentrated under reduced pressure. Purification of the residue by column chromatography on silica gel (silica gel 60—Merck, particle size: 0.04 to 0.063 mm) using the mobile phase ethyl acetate gives 15.9 g (52% of theory) of 4-[[(6-chloropyridin-3-yl)methyl](2,2-difluoroethyl)amino]furan-2(5H)-one.

후처리

  1. temperatureunder reflux for 2 hours
  2. concentrationThe reaction mixture is concentrated under reduced pressure
  3. washthe mixture is washed successively twice with 1 N aqueous hydrochloric acid, twice with 1 N aqueous sodium hydroxide solution and once with saturated sodium chloride solution
  4. dry with materialThe organic phase is dried over sodium sulphate
  5. concentrationconcentrated under reduced pressure
  6. customPurification of the residue by column chromatography on silica gel (silica gel 60—Merck, particle size: 0.04 to 0.063 mm)

출처 및 근거

ORD 기록
ord-a6ec973acc3449db9ba32026c195b3f0
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08546577B2

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