Potassium Carbonate → 4-[(3,4-Dichlorobenzyl)oxy]-2,5-difluoro-N-(methylsulfonyl)benzamide

HRID 508407ノート

反応式

HRID 508407 の反応式
[F:1][C:2]1[CH:14]=[C:13]([OH:15])[C:12]([F:16])=[CH:11][C:3]=1[C:4]([NH:6][S:7]([CH3:10])(=[O:9])=[O:8])=[O:5].Br[CH2:18][C:19]1[CH:24]=[CH:23][C:22]([Cl:25])=[C:21]([Cl:26])[CH:20]=1.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O>[Cl:26][C:21]1[CH:20]=[C:19]([CH:24]=[CH:23][C:22]=1[Cl:25])[CH2:18][O:15][C:13]1[C:12]([F:16])=[CH:11][C:3]([C:4]([NH:6][S:7]([CH3:10])(=[O:8])=[O:9])=[O:5])=[C:2]([F:1])[CH:14]=1

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 6397264-(Bromomethyl)-1,2-dichlorobenzeneHCID 580424162,5-difluoro-4-hydroxy-N-(methylsulfonyl)benzamide

生成物 1

HCID 566445294-[(3,4-Dichlorobenzyl)oxy]-2,5-difluoro-N-(methylsulfonyl)benzamide収率 67%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

実験手順

To a solution of 2,5-Difluoro-4-hydroxy-N-(methylsulfonyl)benzamide (Preparation 18 10.6 g, 42.2 mmol) in DMSO (53 mL) was added 4-(bromomethyl)-1,2-dichlorobenzene (10.63 g, 44.3 mmol) and potassium carbonate (11.66 g, 84.4 mmol) and the reaction stirred at ambient temperature for 18 hours. The reaction was quenched with aqueous hydrogen chloride solution (1 M, 100 mL) and water (100 mL). The resulting off-white precipitate was stirred at room temperature for 1 hour, filtered and washed with water (3×100 mL). The resulting pale yellow solid was suspended in acetone (106 mL) and heated at reflux for 1 hour. The suspension was then cooled to room temperature and filtered to yield the first crop of the crude title compound as a white solid (11.6 g, 67%).

後処理

  1. customThe reaction was quenched with aqueous hydrogen chloride solution (1 M, 100 mL) and water (100 mL)
  2. stirringThe resulting off-white precipitate was stirred at room temperature for 1 hour
  3. filtrationfiltered
  4. washwashed with water (3×100 mL)
  5. temperatureheated
  6. temperatureat reflux for 1 hour
  7. temperatureThe suspension was then cooled to room temperature
  8. filtrationfiltered

出典と根拠

ORDレコード
ord-35fb45b03b59436ea88df9f1e25f72f3
出典データセット
uspto-grants-2015_08
特許番号
US09096500B2

反応ノート

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