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 2120082노트

반응식

HRID 2120082 반응식
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]

참가 물질

6

반응물 3

HCID 6372ChlorodifluoromethaneHCID 11430Potassium CarbonateHCID 136352415HCID 136352415, 화합물

생성물 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 Methylester수율 109%

시약·촉매·용매 2

HCID 74236Tetrabutylammonium Bromide촉매HCID 6228Dimethylformamide용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-0e40463f53a548a9957613493408b85a
출처 데이터셋
uspto-grants-2004_02
특허 번호
US06689773B2

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