Phenyl isocyanate → {1-[(Anilinocarbonyl)amino]cyclohexyl}acetic acid

HRID 550288ノート

反応式

HRID 550288 の反応式
[NH2:1][C:2]1([CH2:8][C:9]([OH:11])=[O:10])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.[OH-].[Na+].[C:14]1([N:20]=[C:21]=[O:22])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>O1CCOCC1.O>[NH:20]([C:21]([NH:1][C:2]1([CH2:8][C:9]([OH:11])=[O:10])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1)=[O:22])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

参加物

6

反応物 3

HCID 7672Phenyl isocyanateHCID 14798Sodium Hydroxide2 回HCID 44266932-(1-Aminocyclohexyl)acetic acid hydrochloride

生成物 1

HCID 57847120{1-[(Anilinocarbonyl)amino]cyclohexyl}acetic acid収率 55.7%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
40 °C

実験手順

To a solution of (1-aminocyclohexyl)acetic acid (0.232 mg, 1.48 mmol) in a mixture of 1,4-dioxane (9 ml) and water (3 ml) was added 30% aqueous sodium hydroxide solution to pH 9. Phenylisocyanate (0.24 ml, 2.22 mmol) was added dropwise at 35° C. and 30% aqueous sodium hydroxide solution was added to adjust the solution to pH9. The reaction mixture was stirred at 40° C. for 1.5 hrs and concentrated under reduced pressure. 5N Hydrochloric acid was added to acidify the solution (pH3) and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine and dried (over anhydrous MgSO4). After concentration under reduced pressure, the precipitated solid was collected by filtration and washed with diisopropy ether to give the title compound (0.228 g) as a colorless powder with contamination.

後処理

  1. concentrationconcentrated under reduced pressure
  2. addition5N Hydrochloric acid was added
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with saturated brine
  5. dry with materialdried (over anhydrous MgSO4)
  6. concentrationAfter concentration under reduced pressure
  7. filtrationthe precipitated solid was collected by filtration
  8. washwashed with diisopropy ether

出典と根拠

ORDレコード
ord-fb0ae12249724eecae9fa971d3c4c9d9
出典データセット
uspto-grants-2011_05
特許番号
US07943770B2

反応ノート

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