Dichloromethane → Pyriprole

HRID 2222263ノート

反応式

HRID 2222263 の反応式
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[C:4]([Cl:12])[C:3]=1[N:13]1[C:17]([NH:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=2)=[CH:16][C:15]([C:26]#[N:27])=[N:14]1.ClCCl.[F:31][CH:32]([F:35])[S:33]Cl>C(OCC)(=O)C>[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:10])([F:11])[F:9])[CH:5]=[C:4]([Cl:12])[C:3]=1[N:13]1[C:17]([NH:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=2)=[C:16]([S:33][CH:32]([F:35])[F:31])[C:15]([C:26]#[N:27])=[N:14]1

参加物

5

反応物 3

HCID 6344Dichloromethane2 回HCID 114184771-(2,6-Dichloro-4-trifluoromethylphenyl)-5-(pyridin-2-ylmethylamino)pyrazole-3-carbonitrileHCID 22618524(Chlorosulfanyl)(difluoro)methane

生成物 1

HCID 12056859Pyriprole収率 90%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

Under a nitrogen atmosphere, 500 mg (1.21 mmol) of 1-(2,6-dichloro-4-trifluoromethylphenyl)-5-(pyridin-2-ylmethylamino)pyrazole-3-carbonitrile was suspended into 5.0 mL of dried dichloromethane, and 2.0 mL of dried dichloromethane containing 180 mg (1.52 mmol, 1.25 eq.) of difluoromethylsulfenyl chloride was added dropwise thereto under stirring at room temperature, followed by reaction for 2 hours. Ethyl acetate (100 mL) was added thereto, and the organic layer was washed successively with 20 mL of a saturated aqueous sodium hydrogen carbonate solution and 20 mL of water, followed by drying over anhydrous magnesium sulfate. After magnesium sulfate was filtered off, the solvent was removed by distillation under reduced pressure and the crude product was recrystallized from a mixed solvent of hexane/ethyl acetate (3/1) to thereby obtain 535 mg of 1-(2,6-dichloro-4-trifluoromethylphenyl)-4-difluoromethylthio-5-(pyridin-2-ylmethylamino)pyrazole-3-carbonitrile (yield: 90%, purity: 96%).

後処理

  1. additionwas added dropwise
  2. customfollowed by reaction for 2 hours
  3. washthe organic layer was washed successively with 20 mL of a saturated aqueous sodium hydrogen carbonate solution and 20 mL of water
  4. dry with materialby drying over anhydrous magnesium sulfate
  5. filtrationAfter magnesium sulfate was filtered off
  6. customthe solvent was removed by distillation under reduced pressure
  7. customthe crude product was recrystallized from a mixed solvent of hexane/ethyl acetate (3/1)

出典と根拠

ORDレコード
ord-5875112d14ee409783e3c709833b32c0
出典データセット
uspto-grants-2008_05
特許番号
US07371768B2

反応ノート

読み込み中…