N,N-Dimethylaniline → Benzyl 4-(2-oxo-1-pyrrolidinyl)phenylcarbamate

HRID 499733

반응식

HRID 499733 반응식
Cl[C:2]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:3].[NH2:12][C:13]1[CH:18]=[CH:17][C:16]([N:19]2[CH2:23][CH2:22][CH2:21][C:20]2=[O:24])=[CH:15][CH:14]=1.CN(C)C1C=CC=CC=1.C(OCC)(=O)C>O1CCCC1>[O:24]=[C:20]1[CH2:21][CH2:22][CH2:23][N:19]1[C:16]1[CH:17]=[CH:18][C:13]([NH:12][C:2](=[O:3])[O:4][CH2:5][C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)=[CH:14][CH:15]=1

참가 물질

6

반응물 4

HCID 949N,N-DimethylanilineHCID 8857Ethyl AcetateHCID 10387Benzyl chloroformateHCID 676146Pyrrolidinone, (4-aminophenyl)-

생성물 1

HCID 7686496Benzyl 4-(2-oxo-1-pyrrolidinyl)phenylcarbamate수율 73.8%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
-20 °C

실험 절차

4.27 g (25.03 mmol) of benzyl chloroformate are slowly added to 4 g (22.7 mmol) of 1-(4-aminophenyl)pyrrolidin-2-one and 3.6 ml (28.4 mmol) of N,N-dimethylaniline in 107 ml of tetrahydrofuran at −20° C. The mixture is stirred at −20° C. for 30 minutes and then allowed to reach room temperature. 0.5 l of ethyl acetate is added, and the organic phase is washed with 0.5 l of saturated NaCl solution. The removed organic phase is dried with MgSO4, and the solvent is evaporated in vacuo. The residue is triturated with diethyl ether and filtered off with suction. 5.2 g (73.8% of theory) of benzyl 4-(2-oxo-1-pyrrolidinyl)phenylcarbamate are obtained as pale beige crystals with a melting point of 174° C.

후처리

  1. customto reach room temperature
  2. washthe organic phase is washed with 0.5 l of saturated NaCl solution
  3. dry with materialThe removed organic phase is dried with MgSO4
  4. customthe solvent is evaporated in vacuo
  5. customThe residue is triturated with diethyl ether
  6. filtrationfiltered off with suction

출처 및 근거

ORD 기록
ord-b678ad7d47524d1ab57465d1e6ea7d61
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07767702B2

연결된 노트

불러오는 중…