2-Mercaptobenzoic Acid → 2-(4-Methoxyphenylthio)benzoic acid

HRID 2373114

反応式

HRID 2373114 の反応式
[C:1]([OH:10])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[SH:4].I[C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=1.C(=O)([O-])[O-].[K+].[K+]>[Cu].CN1CCCC1=O>[CH3:19][O:18][C:15]1[CH:16]=[CH:17][C:12]([S:4][C:3]2[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=2[C:1]([OH:10])=[O:9])=[CH:13][CH:14]=1

参加物

6

反応物 3

HCID 54432-Mercaptobenzoic AcidHCID 11430Potassium CarbonateHCID 696764-Iodoanisole

生成物 1

HCID 28248782-(4-Methoxyphenylthio)benzoic acid

試薬・触媒・溶媒 2

HCID 23978Copper触媒HCID 13387N-methyl-2-pyrrolidone溶媒

反応条件

温度
165 °C

実験手順

First, 2-(4-methoxyphenylthio)benzoic acid was prepared. A stirred mixture of thiosalicylic acid (10.0 g, 65 mmol), 4-iodoanisole (15.18 g, 65 mmol), potassium carbonate (19.72 g, 143 mmol), copper powder (0.82 g, 13 mmol), and N-methylpyrrolidinone (100 mL) was deaerated by sparging with nitrogen for 10 min, heated at 165° C. for 18 h, and then cooled to ambient. The reaction mixture was poured onto a mixture of 500 g of ice plus 40 mL or concentrated HCl. The resulting precipitate was collected, washed with water, and dried. The product was purified by recrystallization from a mixture of water, ethanol, and tetrahydrofuran. A white powder was obtained, mass: 12.06 g (71% of theory).

後処理

  1. customby sparging with nitrogen for 10 min
  2. temperaturecooled
  3. additionThe reaction mixture was poured onto a mixture of 500 g of ice plus 40 mL or concentrated HCl
  4. customThe resulting precipitate was collected
  5. washwashed with water
  6. customdried
  7. customThe product was purified by recrystallization from a mixture of water, ethanol, and tetrahydrofuran
  8. customA white powder was obtained

出典と根拠

ORDレコード
ord-aff65ac74f8440e3ac3a2bece001f2f0
出典データセット
uspto-grants-2008_12
特許番号
US07459263B2

関連ノート

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