Potassium Carbonate → 4-[2-(Dimethylamino)ethylthio]-benzoic acid

HRID 131282

反応式

HRID 131282 の反応式
F[C:2]1[CH:14]=[CH:13][C:5]([C:6]([O:8]C(C)(C)C)=[O:7])=[CH:4][CH:3]=1.Cl.[CH3:16][N:17]([CH3:21])[CH2:18][CH2:19][SH:20].C(=O)([O-])[O-].[K+].[K+]>CS(C)=O.O>[CH3:16][N:17]([CH3:21])[CH2:18][CH2:19][S:20][C:2]1[CH:3]=[CH:4][C:5]([C:6]([OH:8])=[O:7])=[CH:13][CH:14]=1

参加物

6

反応物 3

HCID 11430Potassium CarbonateHCID 25798Captamine HydrochlorideHCID 2736444Tert-butyl 4-fluorobenzoate

生成物 1

HCID 167872194-[2-(Dimethylamino)ethylthio]-benzoic acid収率 110.3%

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 962Water溶媒

反応条件

温度
80 °C

実験手順

A suspension of tert-butyl 4-fluorobenzoate (300 mg), 2-(dimethylamino)-ethanethiol hydrochloride (420 mg), and potassium carbonate (620 mg) in dimethylsulfoxide (3.0 mL) is stirred at 80° C. for 4 hours. The reaction mixture is diluted with water and extracted with ethyl acetate. The extract is concentrated in vacuo and to the residue is added 4N HCl-dioxane (1.5 mL). The mixture is stirred at room temperature overnight. The reaction mixture is diluted with ether and the precipitated crystals are collected by filtration to give 4-[2-(dimethylamino)ethylthio]-benzoic acid (380 mg, yield; 99%) as colorless crystals. MS (APCI) m/z; 226 [M+H]+

後処理

  1. extractionextracted with ethyl acetate
  2. concentrationThe extract is concentrated in vacuo and to the residue
  3. additionis added 4N HCl-dioxane (1.5 mL)
  4. stirringThe mixture is stirred at room temperature overnight
  5. additionThe reaction mixture is diluted with ether
  6. filtrationthe precipitated crystals are collected by filtration

出典と根拠

ORDレコード
ord-a153716750a84def84a3a8d919f29795
出典データセット
uspto-grants-2008_06
特許番号
US07384952B2

関連ノート

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