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 1625111ノート

反応式

HRID 1625111 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 111,2-Dichloroethane溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
160 °C

実験手順

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%).

後処理

  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%

出典と根拠

ORDレコード
ord-ca08964299a3430db4e3d459535d80cb
出典データセット
uspto-grants-2014_07
特許番号
US08779157B2

反応ノート

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