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

HRID 1262186노트

반응식

HRID 1262186 반응식
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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 180Acetone용매

반응 조건

온도
40 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-8ceeefd2ff06415c9579861efdd54dcd
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08471005B2

반응 노트

불러오는 중…