Chlorodifluoromethane → 2-Chloro-4-fluoro-5-[4-(difluoromethyl)-4,5-dihydro-3-methyl-5-oxo-1H-1,2,4-triazol-1-yl]-benzoic Acid Methylester

HRID 1861624ノート

反応式

HRID 1861624 の反応式
Cl[CH:2]([F:4])[F:3].[CH3:5][O:6][C:7](=[O:23])[C:8]1[CH:13]=[C:12]([N:14]2[C:18](=[O:19])[NH:17][C:16]([CH3:20])=[N:15]2)[C:11]([F:21])=[CH:10][C:9]=1[Cl:22].C(=O)([O-])[O-].[K+].[K+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C)C=O>[CH3:5][O:6][C:7](=[O:23])[C:8]1[CH:13]=[C:12]([N:14]2[C:18](=[O:19])[N:17]([CH:2]([F:4])[F:3])[C:16]([CH3:20])=[N:15]2)[C:11]([F:21])=[CH:10][C:9]=1[Cl:22]

参加物

6

反応物 3

HCID 6372ChlorodifluoromethaneHCID 11430Potassium CarbonateHCID 136352415HCID 136352415、化合物

生成物 1

HCID 120971882-Chloro-4-fluoro-5-[4-(difluoromethyl)-4,5-dihydro-3-methyl-5-oxo-1H-1,2,4-triazol-1-yl]-benzoic Acid Methylester収率 109%

試薬・触媒・溶媒 2

HCID 74236Tetrabutylammonium Bromide触媒HCID 6228Dimethylformamide溶媒

実験手順

An excess of chlorodifluoromethane (97 g) was bubbled into a mixture of triazolinone from step 2 (7.04 g, 24.6 mmol), tetrabutylammonium bromide (9.67 g, 30.0 mmol), potassium carbonate (16.6 g, 122 mmol) and dimethylformamide (200 ml) in such a way that T<36° C. over a period of 30 minutes. The mixture was cooled and filtered. The filtrate was concentrated under reduced presssure and the residue partitioned between water and methylene chloride. The organic layer was washed with water, dried and concentrated under reduced pressure to give a dark oil (9.00 g), which was chromatographed on silica gel (eluent: ethyl acetate/hexane) to give the title compound. Yield: 1.48 g (17.9%).

後処理

  1. temperatureThe mixture was cooled
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated under reduced presssure
  4. customthe residue partitioned between water and methylene chloride
  5. washThe organic layer was washed with water
  6. customdried
  7. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-597378f2d84a4e17a6b67057d461076b
出典データセット
uspto-grants-2003_03
特許番号
US06534492B2

反応ノート

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