Allylamine → 3-((Prop-2-en-1-yl)sulfamoyl)benzoic acid

HRID 518642ノート

反応式

HRID 518642 の反応式
Cl[S:2]([C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][CH:13]=1)[C:8]([OH:10])=[O:9])(=[O:4])=[O:3].[CH2:14]([NH2:17])[CH:15]=[CH2:16].[OH-].[Na+]>C1COCC1.Cl>[CH2:14]([NH:17][S:2]([C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][CH:13]=1)[C:8]([OH:10])=[O:9])(=[O:4])=[O:3])[CH:15]=[CH2:16]

参加物

6

反応物 3

HCID 7853AllylamineHCID 14798Sodium HydroxideHCID 77641Benzoic acid, 3-(chlorosulfonyl)-

生成物 1

HCID 2574683-((Prop-2-en-1-yl)sulfamoyl)benzoic acid収率 95.1%

試薬・触媒・溶媒 2

HCID 313Hydrochloric Acid溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 3-(chlorosulfonyl)benzoic acid (5 g, 22.66 mmol) in THF (50.4 mL) at 0° C. was added allylamine (2.038 mL, 27.2 mmol) followed by NaOH (1N aqueous) (49.9 mL, 49.9 mmol). The mixture was allowed to warm to RT over 1 hour and stirred an additional 16 hours. The mixture was diluted with 1N HCl (250 mL), and the aqeuous layer was extracted with EtOAc (300 mL). The organic layer was dried over sodium sulfate and concentrated to dryness to afford 3-(N-allylsulfamoyl)benzoic acid as white solid (5.2 g, 95% yield). MS m/z=242.0 [M+H]. Calc'd for C10H11NO4S: 241.0.

後処理

  1. extractionthe aqeuous layer was extracted with EtOAc (300 mL)
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. concentrationconcentrated to dryness

出典と根拠

ORDレコード
ord-49a46971595040cf8faba1ce531b31fa
出典データセット
uspto-grants-2015_08
特許番号
US09115127B2

反応ノート

読み込み中…