Water → alpha-acetyl-2,4-dichloro-N-(2,4-difluorophenyl)benzeneethanethioamide

HRID 2174625ノート

反応式

HRID 2174625 の反応式
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[N:9]=[C:10]=[S:11].[H-].[Na+].[Cl:14][C:15]1[CH:20]=[C:19]([Cl:21])[CH:18]=[CH:17][C:16]=1[CH2:22][C:23](=[O:25])[CH3:24].O>O1CCCC1>[C:23]([CH:22]([C:16]1[CH:17]=[CH:18][C:19]([Cl:21])=[CH:20][C:15]=1[Cl:14])[C:10](=[S:11])[NH:9][C:3]1[CH:4]=[CH:5][C:6]([F:8])=[CH:7][C:2]=1[F:1])(=[O:25])[CH3:24]

参加物

6

反応物 4

HCID 962WaterHCID 24758Sodium hydrideHCID 5188792,4-Difluoro-1-isothiocyanatobenzeneHCID 27341022,4-Dichlorophenylacetone

生成物 1

HCID 86660671alpha-acetyl-2,4-dichloro-N-(2,4-difluorophenyl)benzeneethanethioamide収率 32.1%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
7.5 °C

実験手順

2,4-Difluorophenyl isothiocyanate (0.27 mL, 2.0 mmol) was added to a stirred suspension of sodium hydride (60% in mineral oil) (112 mg, 2.8 mmol) in anhydrous tetrahydrofuran (4 mL) cooled in an ice-water bath under a nitrogen atmosphere. A solution of (2,4-dichlorophenyl)-2-propanone (570 mg, 2.8 mmol) in tetrahydrofuran (4 mL) was added dropwise over 5 min. The resultant yellow solution was stirred at 5-10° C. for 1 h. Water (10 mL) was carefully added, and the reaction mixture was extracted with ethyl acetate (10 mL). The aqueous phase was acidified to pH 3 with 1 N aqueous HCl, then extracted with ethyl acetate (20 mL). The organic extract was washed with water (10 mL) and brine (10 mL), dried over MgSO4, and concentrated to leave a solid. The solid was triturated with hexanes/ethyl acetate (2:1), collected on a glass frit, and air-dried to give the title compound as a white solid (240 mg). MS: 373 amu (AP+).

後処理

  1. temperaturecooled in an ice-water bath under a nitrogen atmosphere
  2. extractionthe reaction mixture was extracted with ethyl acetate (10 mL)
  3. extractionextracted with ethyl acetate (20 mL)
  4. extractionThe organic extract
  5. washwas washed with water (10 mL) and brine (10 mL)
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated
  8. customto leave a solid
  9. customThe solid was triturated with hexanes/ethyl acetate (2:1)
  10. customcollected on a glass frit
  11. customair-dried

出典と根拠

ORDレコード
ord-25d0e0fc216445649e5384f981c31306
出典データセット
uspto-grants-2015_06
特許番号
US09062005B2

反応ノート

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