Furfurylamine → N-(furan-2-ylmethyl)methanesulfonamide

HRID 1776170노트

반응식

HRID 1776170 반응식
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[CH2:6]([NH2:12])[C:7]1[O:11][CH:10]=[CH:9][CH:8]=1.C(N(CC)CC)C>C(Cl)Cl.C(OCC)(=O)C>[O:11]1[CH:10]=[CH:9][CH:8]=[C:7]1[CH2:6][NH:12][S:2]([CH3:1])(=[O:4])=[O:3]

참가 물질

6

반응물 3

HCID 3438FurfurylamineHCID 8471TriethylamineHCID 31297Methanesulfonyl chloride

생성물 1

HCID 240162N-(furan-2-ylmethyl)methanesulfonamide수율 89.7%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

실험 절차

Methanesulfonyl chloride (3.2 mL, 42 mmol) was slowly added to a stirring solution of furfurylamine (4.2 g, 43.2 mmol) and triethylamine (6 mL, 43 mmol) in anhydrous methylene chloride (110 mL). The reaction was stirred overnight at ambient temperature and then diluted with ethyl acetate. The organic solution was successively washed with 1N aqueous hydrochloric acid three times, saturated aqueous sodium bicarbonate and saturated aqueous sodium chloride solutions, dried (anhydrous sodium sulfate), and filtered. The solution was concentrated under reduced pressure to give the desired product as a tan liquid (6.6 g, 89%). 1H NMR (CDCl3, 300 MHz) δ 7.39-7.38 (m, 1H), 6.33-6.31 (m, 2H), 5.02 (br s, 1H), 4.33-4.31 (d, 2H, J=6 Hz).

후처리

  1. washThe organic solution was successively washed with 1N aqueous hydrochloric acid three times, saturated aqueous sodium bicarbonate and saturated aqueous sodium chloride solutions
  2. dry with materialdried (anhydrous sodium sulfate)
  3. filtrationfiltered
  4. concentrationThe solution was concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-a2b7407b2db04f298980a894db6169a3
출처 데이터셋
uspto-grants-2016_02
특허 번호
US09265772B2

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