Cesium carbonate → HCID 66666047, 화합물

HRID 474242

반응식

HRID 474242 반응식
[OH:1][C:2]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:20][CH2:21][CH2:22][CH2:23][NH:24][C:25](=[O:31])[O:26][C:27]([CH3:30])([CH3:29])[CH3:28]>CN(C=O)C>[C:4]([C:3]1[CH:6]=[CH:7][C:8]([N+:10]([O-:12])=[O:11])=[CH:9][C:2]=1[O:1][CH2:20][CH2:21][CH2:22][CH2:23][NH:24][C:25](=[O:31])[O:26][C:27]([CH3:30])([CH3:29])[CH3:28])#[N:5]

참가 물질

5

반응물 3

HCID 10796Cesium carbonateHCID 2861482-Hydroxy-4-nitrobenzonitrileHCID 10868765tert-butyl N-(4-bromobutyl)carbamate

생성물 1

HCID 66666047HCID 66666047, 화합물수율 52%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a stirred mixture of 2-hydroxy-4-nitrobenzonitrile (2 g, 12.19 mmol), cesium carbonate (6 g, 18.29 mmol) and DMF (20 mL) was added tert-butyl 4-bromobutylcarbamate (4.59 g, 18.29 mmol). The reaction mixture was stirred at room temperature for 18 h. The solvent was removed under reduced pressure and the residue was dissolved in ethyl acetate (100 mL), and washed with brine (2×50 mL). The organic layer was dried with anhydrous sodium sulphate and concentrated in vacuo to give tert-butyl 4-(2-cyano-5-nitrophenoxy)butylcarbamate (2.1 g, 52%) as a light yellow solid. LC-MS (M+H)+=335.0. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.07 (1H, d, J=8.4 Hz), 7.96 (1H, s), 7.90 (2H, d, J=8.8 Hz), 6.84 (1H, br s), 4.30 (2H, t, J=6.4 Hz), 3.53 (2H, t, J=6.4 Hz), 2.98-2.89 (2H, m), 1.81-1.76 (2H, m), 1.48 (9H, s).

후처리

  1. customThe solvent was removed under reduced pressure
  2. dissolutionthe residue was dissolved in ethyl acetate (100 mL)
  3. washwashed with brine (2×50 mL)
  4. dry with materialThe organic layer was dried with anhydrous sodium sulphate
  5. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-70cadaf387c544caa779c2e0e4fb28e9
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08637523B2

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