Water → Flupyradifurone

HRID 1037639ノート

反応式

HRID 1037639 の反応式
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

参加物

6

反応物 3

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

生成物 1

HCID 16752772Flupyradifurone収率 52%

試薬・触媒・溶媒 2

HCID 6101p-Toluenesulfonic acid触媒HCID 1140Toluene溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-a6ec973acc3449db9ba32026c195b3f0
出典データセット
uspto-grants-2013_10
特許番号
US08546577B2

反応ノート

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