1-Aminocyclohexanecarboxylic acid → 1-[(2-Furanylcarbonyl)amino]cyclohexanecarboxylic acid

HRID 73818

반응식

HRID 73818 반응식
[NH2:1][C:2]1([C:8]([OH:10])=[O:9])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.[OH-].[Na+].[O:13]1[CH:17]=[CH:16][CH:15]=[C:14]1[C:18](Cl)=[O:19].C(OCC)(=O)C>O>[O:13]1[CH:17]=[CH:16][CH:15]=[C:14]1[C:18]([NH:1][C:2]1([C:8]([OH:10])=[O:9])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1)=[O:19]

참가 물질

6

반응물 4

HCID 13661-Aminocyclohexanecarboxylic acidHCID 8857Ethyl AcetateHCID 14798Sodium Hydroxide2회HCID 682422-Furancarbonyl chloride

생성물 1

HCID 174552541-[(2-Furanylcarbonyl)amino]cyclohexanecarboxylic acid수율 237.3%

시약·촉매·용매 1

HCID 962Water용매2회

반응 조건

온도
80 °C

실험 절차

71.6 g (0.5 mol) of 1-aminocyclohexanecarboxylic acid was added to a solution of 20 g (0.5 mol) of sodium hydroxide in 250 ml of water, and the mixture was stirred at 80° C. for 2 hours. The mixture solution was cooled by ice-water, 71.8 g (0.2 mol) of 2-furancarbonyl chloride and a solution of 24 g (0.6 mol) of sodium hydroxide in 100 ml of water were simultaneously added thereto over approximately 1 hour. The reaction solution was slowly returned to room temperature and stirred overnight. After 80 ml of ethyl acetate was added to the reaction solution and the mixture was stirred for 1 hour, the insolubles were removed by filtration. The aqueous layer was separately collected, 49 ml of concentrated hydrochloric acid was added thereto under ice-cooling. The precipitated crystal was collected by filtration and dried-under reduced pressure to obtain 112.6 g (95%) of the title compound.

후처리

  1. waitover approximately 1 hour
  2. customwas slowly returned to room temperature
  3. stirringstirred overnight
  4. stirringthe mixture was stirred for 1 hour
  5. customthe insolubles were removed by filtration
  6. customThe aqueous layer was separately collected
  7. addition49 ml of concentrated hydrochloric acid was added
  8. temperatureunder ice-cooling
  9. filtrationThe precipitated crystal was collected by filtration and dried-under reduced pressure

출처 및 근거

ORD 기록
ord-d2bb77af91dd4b7eae884941754e58c0
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08829209B2

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