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

HRID 1071166노트

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HRID 1071166 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

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온도
0 °C

실험 절차

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+).

후처리

  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

출처 및 근거

ORD 기록
ord-74d6fcc8e0594cda80551e6173ffc366
출처 데이터셋
uspto-grants-2005_06
특허 번호
US06903218B2

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