Phenyl isocyanate → phenyl-carbamic acid 2-(2-oxo-2,3-dihydro-1H-indol-4-yl)-ethyl ester

HRID 2120245

반응식

HRID 2120245 반응식
[C:1]1([N:7]=[C:8]=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH:10][CH2:11][CH2:12][C:13]1[CH:21]=[CH:20][CH:19]=[C:18]2[C:14]=1[CH2:15][C:16](=[O:22])[NH:17]2.[OH-].[Na+]>O1CCCC1.CN(C)C=O.N1C=CC=CC=1>[O:22]=[C:16]1[CH2:15][C:14]2[C:18](=[CH:19][CH:20]=[CH:21][C:13]=2[CH2:12][CH2:11][O:10][C:8](=[O:9])[NH:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[NH:17]1

참가 물질

7

반응물 3

HCID 7672Phenyl isocyanateHCID 14798Sodium HydroxideHCID 109430044-(2-Hydroxyethyl)indolin-2-one

생성물 1

HCID 9860973phenyl-carbamic acid 2-(2-oxo-2,3-dihydro-1H-indol-4-yl)-ethyl ester수율 80.4%

시약·촉매·용매 3

HCID 1049Pyridine촉매HCID 6228Dimethylformamide용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
70 °C

실험 절차

Phenyl isocyanate (0.652 mL, 6 mmol) was added dropwise to a stirred mixture of 4-(2-hydroxy-ethyl)-1,3-dihydro-indol-2-one (709 mg, 4 mmol) in tetrahydrofuran (8 mL), dimethylforamide (2 mL) and pyridine (3 drops). The mixture was heated at 70° C. for 15 hours. The reaction was cooled, poured into 1 N sodium hydroxide solution (100 mL) and extracted with ethyl acetate (200 mL). The organic layer was washed with 1 N hydrochloric acid (100 mL) and brine, dried over anhydrous sodium sulfate and concentrated. The residue was recrystallized from methanol/ethyl acetate/hexane to give 953 mg (80%) of phenyl-carbamic acid 2-(2-oxo-2,3-dihydro-1H-indol-4-yl)-ethyl ester as an off-white powder.

후처리

  1. temperatureThe reaction was cooled
  2. extractionextracted with ethyl acetate (200 mL)
  3. washThe organic layer was washed with 1 N hydrochloric acid (100 mL) and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customThe residue was recrystallized from methanol/ethyl acetate/hexane

출처 및 근거

ORD 기록
ord-5bf1c48907b346648b4bfb3ef23a9029
출처 데이터셋
uspto-grants-2004_02
특허 번호
US06689806B1

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