1,8-Diazabicyclo(5.4.0)undec-7-ene → 2-(2-chloro-4-nitrophenyl)tetrahydro-1H-imidazo[5,1-c][1,4]oxazine-1,3(2H)-dione

HRID 1625111노트

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HRID 1625111 반응식
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH:2]1[C:7]([OH:9])=O.C1CCN2C(=NCCC2)CC1.[Cl:21][C:22]1[CH:27]=[C:26]([N+:28]([O-:30])=[O:29])[CH:25]=[CH:24][C:23]=1[N:31]=[C:32]=[O:33]>ClCCCl.C(Cl)Cl>[Cl:21][C:22]1[CH:27]=[C:26]([N+:28]([O-:30])=[O:29])[CH:25]=[CH:24][C:23]=1[N:31]1[C:7](=[O:9])[CH:2]2[CH2:3][O:4][CH2:5][CH2:6][N:1]2[C:32]1=[O:33]

참가 물질

6

반응물 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 33401523-Morpholinecarboxylic acidHCID 46142212-Chloro-4-nitrophenyl isocyanate

생성물 1

HCID 670602392-(2-chloro-4-nitrophenyl)tetrahydro-1H-imidazo[5,1-c][1,4]oxazine-1,3(2H)-dione수율 54.2%

시약·촉매·용매 2

HCID 111,2-Dichloroethane용매HCID 6344Dichloromethane용매

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온도
160 °C

실험 절차

To a stirred solution of 3-morphline carboxylic acid (0.100 g; 0.627 mmol), DBU (187 μL; 1.25 mmol) in 1,2-dichloroethane (2.8 mL) was added 2-chloro-4-nitrophenylisocyanate (0.149 g; 0.752 mmol) and the resulting mixture was heated at 160° C. in the microwave for 10 min. The reaction was diluted with methylene chloride (15 mL), washed with 1N HCl (10 mL), sat. NaHCO3 (10 mL) and concentrated under vacuum to give the crude product. The residue was purified by column chromatography eluting with ethyl acetate/hexanes 0 to 40% to give 106 mg of 2-(2-chloro-4-nitrophenyl)tetrahydro-1H-imidazo[5,1-c][1,4]oxazine-1,3(2H)-dione, 1.1.21, (54%).

후처리

  1. washwashed with 1N HCl (10 mL), sat. NaHCO3 (10 mL)
  2. concentrationconcentrated under vacuum
  3. customto give the crude product
  4. customThe residue was purified by column chromatography
  5. washeluting with ethyl acetate/hexanes 0 to 40%

출처 및 근거

ORD 기록
ord-ca08964299a3430db4e3d459535d80cb
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08779157B2

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