Triethylamine → 3-Chloro-5-difluoromethoxy-N-methoxy-N-methylbenzamide

HRID 1717464ノート

反応式

HRID 1717464 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([O:11][CH:12]([F:14])[F:13])[CH:10]=1)[C:5]([OH:7])=O.C(Cl)(=O)C(Cl)=O.[CH3:21][NH:22][O:23][CH3:24].C(N(CC)CC)C>C(Cl)Cl.CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([O:11][CH:12]([F:14])[F:13])[CH:10]=1)[C:5]([N:22]([O:23][CH3:24])[CH3:21])=[O:7]

参加物

7

反応物 4

HCID 8471TriethylamineHCID 14232N,O-DimethylhydroxylamineHCID 65578Oxalyl chlorideHCID 219046063-Chloro-5-(difluoromethoxy)benzoic acid

生成物 1

HCID 219046583-Chloro-5-difluoromethoxy-N-methoxy-N-methylbenzamide収率 93.8%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide触媒HCID 6344Dichloromethane溶媒

実験手順

3-Chloro-5-difluoromethoxybenzoic acid (1.8 g, 8 mmol; see step (iii) above) and oxalyl chloride (1.5 g, 11.8 mmol) were dissolved in methylene chloride (50 mL). DMF (2 drops) was added and the reaction mixture was stirred at ambient temperature for 30 minutes. Then, N,O-dimethylhydroxylamine (1 g, 10.2 mmol) and triethylamine (3 g, 30 mmol) were added and after another 10 minutes stirring at ambient temperature, the reaction mixture was concentrated at reduced pressure. The residue was taken up in ether (100 mL) and water (50 mL). After separation, the organic phase washed with brine, dried over sodium sulphate, filtered and concentrated. This residue was chromatographed on silica (hexane/ethyl acetate 2:1) which gave 2 g, 7.5 mmol (93%) of the sub-title compound.

後処理

  1. stirringstirring at ambient temperature
  2. concentrationthe reaction mixture was concentrated at reduced pressure
  3. customAfter separation
  4. washthe organic phase washed with brine
  5. dry with materialdried over sodium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThis residue was chromatographed on silica (hexane/ethyl acetate 2:1) which

出典と根拠

ORDレコード
ord-9186e66342b04e2a94289a508be26877
出典データセット
uspto-grants-2010_09
特許番号
US07803954B2

反応ノート

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