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 2120082ノート

反応式

HRID 2120082 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 pressure 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 pressure
  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-0e40463f53a548a9957613493408b85a
出典データセット
uspto-grants-2004_02
特許番号
US06689773B2

反応ノート

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