Cesium carbonate → HCID 66666091, 화합물

HRID 474237

반응식

HRID 474237 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][NH:23][C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27]>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][NH:23][C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])#[N:5]

참가 물질

5

반응물 3

HCID 10796Cesium carbonateHCID 2861482-Hydroxy-4-nitrobenzonitrileHCID 4460490tert-butyl N-(3-bromopropyl)carbamate

생성물 1

HCID 66666091HCID 66666091, 화합물수율 63.9%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a stirred mixture of 2-hydroxy-4-nitrobenzonitrile (4 g, 24.37 mmol) and cesium carbonate (11.91 g, 36.6 mmol) in DMF (40 mL) was added tert-butyl 3-bromopropylcarbamate (8.71 g, 36.6 mmol) at room temperature. The reaction mixture was stirred at room temperature for 18 h. The solvent was removed under reduced pressure and the residue was taken in ethyl acetate (250 mL), washed with brine (2×100 mL). The organic layer was dried over anhydrous sodium sulphate and concentrated in vacuo to give tert-butyl 3-(2-cyano-5-nitrophenoxy)propylcarbamate (5 g, 63.8%) as a yellow solid. LC-MS (M+H)+=321.2. 1H NMR (400 MHz, CDCl3) δ ppm 7.89-7.87 (1H, m), 7.81 (1H, s), 7.75 (1H, d, J=8.4 Hz), 4.76 (1H, br s), 4.27-4.24 (2H, t, J=6.4 Hz), 3.40-3.36 (2H, q, J=6.4, 12.8 Hz), 2.15-2.09 (2H, m), 1.43 (9H, s).

후처리

  1. customThe solvent was removed under reduced pressure
  2. washwashed with brine (2×100 mL)
  3. dry with materialThe organic layer was dried over anhydrous sodium sulphate
  4. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-57dcae1c2dce4641bbc3c388fa94fe94
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08637523B2

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