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

HRID 1776170ノート

反応式

HRID 1776170 の反応式
[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]

参加物

6

反応物 3

HCID 3438FurfurylamineHCID 8471TriethylamineHCID 31297Methanesulfonyl chloride

生成物 1

HCID 240162N-(furan-2-ylmethyl)methanesulfonamide収率 89.7%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-a2b7407b2db04f298980a894db6169a3
出典データセット
uspto-grants-2016_02
特許番号
US09265772B2

反応ノート

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