Cesium carbonate → HCID 66666091、化合物

HRID 474237

反応式

HRID 474237 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][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]

参加物

5

反応物 3

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

生成物 1

HCID 66666091HCID 66666091、化合物収率 63.9%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-57dcae1c2dce4641bbc3c388fa94fe94
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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