Water → 1-(3-Cyclopentyl-propyl)-3-(4-nitro-phenyl)-1,3-dihydro-imidazol-2-one

HRID 1071166ノート

反応式

HRID 1071166 の反応式
[CH:1]1([CH2:6][CH2:7][CH2:8][NH:9][CH2:10][CH:11](OC)OC)[CH2:5][CH2:4][CH2:3][CH2:2]1.[N+:16]([C:19]1[CH:24]=[CH:23][C:22]([N:25]=[C:26]=[O:27])=[CH:21][CH:20]=1)([O-:18])=[O:17].FC(F)(F)C(O)=O.O>C(Cl)Cl>[CH:1]1([CH2:6][CH2:7][CH2:8][N:9]2[CH:10]=[CH:11][N:25]([C:22]3[CH:21]=[CH:20][C:19]([N+:16]([O-:18])=[O:17])=[CH:24][CH:23]=3)[C:26]2=[O:27])[CH2:2][CH2:3][CH2:4][CH2:5]1

参加物

6

反応物 4

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 66012Benzene, 1-isocyanato-4-nitro-HCID 187930233-Cyclopentyl-propyl (2,2-dimethoxy-ethyl)-amine

生成物 1

HCID 224717321-(3-Cyclopentyl-propyl)-3-(4-nitro-phenyl)-1,3-dihydro-imidazol-2-one

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

反応条件

温度
0 °C

実験手順

The product from Example 48 (2.6 g, 12.1 mmol) was dissolved in CH2Cl2 (30 mL) and cooled to 0° C. 4-Nitrophenylisocyanate (1.98 g, 12.1 mmol) was added, and the mixture was allowed to warm to 23° C. The reaction was diluted with additional CH2Cl2 (30 mL) and cooled to 0° C. before a 1:1 solution of trifluoroacetic acid and water was added. The biphasic solution was vigorously stirred for 18 hours at ambient temperature. The layers were separated, and the aqueous layer was extracted with CHCl3. The combined organic layers were washed with saturated NaHCO3, brine, dried (MgSO4), and concentrated to a yellow solid. Mp 105-107° C. Rf=0.4 (2:1 hexanes/ethyl acetate); 1H NMR (300 MHz, DMSO-d6) δ 8.30 (d, 2H), 8.11 (d, 2H), 7.26 (d, 1H), 6.91 (d, 1H), 3.57 (t, 2H), 1.71 (m, 3H), 1.63 (m, 2H), 1.47 (m, 4H), 1.24 (m, 2H), 1.03 (m, 2H); MS (CI) m/z 316 (MH+).

後処理

  1. temperatureto warm to 23° C
  2. additionwas added
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with CHCl3
  5. washThe combined organic layers were washed with saturated NaHCO3, brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated to a yellow solid

出典と根拠

ORDレコード
ord-74d6fcc8e0594cda80551e6173ffc366
出典データセット
uspto-grants-2005_06
特許番号
US06903218B2

反応ノート

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