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

HRID 448723

反応式

HRID 448723 の反応式
[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]

参加物

6

反応物 4

HCID 13661-Aminocyclohexanecarboxylic acidHCID 8857Ethyl AcetateHCID 14798Sodium Hydroxide2 回HCID 682422-Furancarbonyl chloride

生成物 1

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

試薬・触媒・溶媒 1

HCID 962Water溶媒2 回

反応条件

温度
80 °C

実験手順

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, and 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 in water were simultaneously added thereto for approximately 1 hour. The reaction solution was slowly returned to room temperature, and it was 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, and 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.

後処理

  1. waitfor approximately 1 hour
  2. customwas slowly returned to room temperature
  3. stirringit was stirred 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
  10. customdried under reduced pressure

出典と根拠

ORDレコード
ord-7949e73b35914194818872c635749423
出典データセット
uspto-grants-2013_07
特許番号
US08481725B2

関連ノート

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