Water → N-(4-difluoromethoxy-3-fluorophenyl)-1-methylcyclopropanecarboxamide

HRID 543574ノート

反応式

HRID 543574 の反応式
[F:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[O:9][CH:10]([F:12])[F:11])[NH2:5].C(N(CC)CC)C.[CH3:20][C:21]1([C:24](Cl)=[O:25])[CH2:23][CH2:22]1.O>C(Cl)Cl>[F:12][CH:10]([F:11])[O:9][C:8]1[CH:7]=[CH:6][C:4]([NH:5][C:24]([C:21]2([CH3:20])[CH2:23][CH2:22]2)=[O:25])=[CH:3][C:2]=1[F:1]

参加物

6

反応物 4

HCID 962WaterHCID 8471TriethylamineHCID 127899391-Methylcyclopropane-1-carbonyl chlorideHCID 132929114-(Difluoromethoxy)-3-fluoroaniline

生成物 1

HCID 13314707N-(4-difluoromethoxy-3-fluorophenyl)-1-methylcyclopropanecarboxamide収率 83.9%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

To a solution of 3-fluoro-4-difluoromethoxyaniline (1.8 g) in methylene chloride (50 ml), triethylamine (1.1 g) was added, and a solution of 1-methylcyclopropanecarbonyl chloride (1.2 g) in methylene chloride was dropwise added thereto while stirring and ice-cooling. After stirring at room temperature for 1 hour, the reaction mixture was admixed with water and extracted with ether. The extract was washed with 1 N hydrochloric acid, sodium hydrogen carbonate solution and saturated sodium chloride solution, dried over anhydrous magnesium sulfate and concentrated. The oily residue (2.5 g) was chromatographed on silica gel and eluted with a mixture of hexane and acetone to give N-(4-difluoromethoxy-3-fluorophenyl)-1-methylcyclopropanecarboxamide (2.2 g). nD24 1.5061.

後処理

  1. temperatureice-cooling
  2. stirringAfter stirring at room temperature for 1 hour
  3. extractionextracted with ether
  4. washThe extract was washed with 1 N hydrochloric acid, sodium hydrogen carbonate solution and saturated sodium chloride solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated
  7. customThe oily residue (2.5 g) was chromatographed on silica gel
  8. washeluted with a mixture of hexane and acetone

出典と根拠

ORDレコード
ord-98c32e5879324ad5b230caa78cffee18
出典データセット
uspto-grants-1984_05
特許番号
US04447260

反応ノート

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