Cesium carbonate → HCID 66666047、化合物

HRID 474242

反応式

HRID 474242 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

HCID 66666047HCID 66666047、化合物収率 52%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-70cadaf387c544caa779c2e0e4fb28e9
出典データセット
uspto-grants-2014_01
特許番号
US08637523B2

関連ノート

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