Potassium Carbonate → (4-((1,1-Dioxidothiomorpholino)methyl)phenyl)boronic acid

HRID 1262186

反応式

HRID 1262186 の反応式
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([B:9]([OH:11])[OH:10])=[CH:5][CH:4]=1.[NH:12]1[CH2:17][CH2:16][S:15](=[O:19])(=[O:18])[CH2:14][CH2:13]1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[B:9]([C:6]1[CH:7]=[CH:8][C:3]([CH2:2][N:12]2[CH2:17][CH2:16][S:15](=[O:19])(=[O:18])[CH2:14][CH2:13]2)=[CH:4][CH:5]=1)([OH:11])[OH:10]

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 27355934-(Bromomethyl)phenylboronic acidHCID 6484228Thiomorpholine 1,1-dioxide

生成物 1

HCID 54970580(4-((1,1-Dioxidothiomorpholino)methyl)phenyl)boronic acid収率 99%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

反応条件

温度
40 °C

実験手順

A suspension of (4-bromomethylphenyl)boronic acid (2.00 g, 9.31 mmol), thiomorpholine 1,1-dioxide (1.50 g, 11.1 mmol), and potassium carbonate (2.60 g, 18.8 mmol) in acetone (25 mL) was stirred at 40° C. for 18 hours. The mixture was cooled to room temperature and the volatiles were evaporated. The residue was suspended in saturated aqueous ammonium chloride (100 mL). The aqueous phase was decanted from the waxy solid, rinsed with water (50 mL), and decanted again. The waxy solid was dissolved in methanol (50 mL), filtered to remove insoluble salts and evaporated to obtain 4-[(4-boronophenyl)methyl]-thiomorpholine 1,1-dioxide as a tan foam (2.48 g). The recovered material was crude by 1HNMR but was used without further purification.

後処理

  1. temperatureThe mixture was cooled to room temperature
  2. customthe volatiles were evaporated
  3. customThe aqueous phase was decanted from the waxy solid
  4. washrinsed with water (50 mL)
  5. customdecanted again
  6. dissolutionThe waxy solid was dissolved in methanol (50 mL)
  7. filtrationfiltered
  8. customto remove insoluble salts
  9. customevaporated

出典と根拠

ORDレコード
ord-8ceeefd2ff06415c9579861efdd54dcd
出典データセット
uspto-grants-2013_06
特許番号
US08471005B2

関連ノート

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