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

HRID 1009928

반응식

HRID 1009928 반응식
[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

참가 물질

6

반응물 3

HCID 7672Phenyl isocyanateHCID 14798Sodium Hydroxide2회HCID 44266932-(1-Aminocyclohexyl)acetic acid hydrochloride

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 312751,4-Dioxane용매

반응 조건

온도
40 °C

실험 절차

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 diisopropyl ether to give the title compound (0.228 g) as a colorless powder with contamination.

후처리

  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 diisopropyl ether

출처 및 근거

ORD 기록
ord-4c46f82b77324daf8eec824c259c7b85
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07973163B2

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