Pyridine → Phenyl 3-cyano-4-(ethylsulfonyl)phenylcarbamate

HRID 735558ノート

反応式

HRID 735558 の反応式
[C:1]1([O:7][C:8](Cl)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:11][C:12]1[CH:13]=[CH:14][C:15]([S:20]([CH2:23][CH3:24])(=[O:22])=[O:21])=[C:16]([CH:19]=1)[C:17]#[N:18].N1C=CC=CC=1>C(Cl)Cl>[C:17]([C:16]1[CH:19]=[C:12]([NH:11][C:8](=[O:9])[O:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:13]=[CH:14][C:15]=1[S:20]([CH2:23][CH3:24])(=[O:22])=[O:21])#[N:18]

参加物

5

反応物 3

HCID 1049PyridineHCID 15891Phenyl chloroformateHCID 598380375-Amino-2-(ethanesulfonyl)benzonitrile

生成物 1

HCID 68818495Phenyl 3-cyano-4-(ethylsulfonyl)phenylcarbamate収率 85%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Phenylchloroformate (0.63 mL, 5 mmol) was added dropwise to a solution of 6B in methylene chloride (10 mL) and pyridine (0.60 mL, 7.1 mmol) at 0° C. After stirring for 1 h, the reaction mixture was partitioned between 1.0 M HCl (150 mL) and EtOAc (150 mL). The layers were separated and the organic phase was washed with saturated NaHCO3, brine, dried over Na2SO4 and concentrated. The crude product was purified by flash chromatography (0% to 100% EtOAc in hexanes) to yield 25A (1.34 g, 85%) as a white solid. 1H NMR (400 MHz, CD3OD) δ ppm 1.32 (t, J=7.45 Hz, 3 H) 3.36 (q, J=7.33 Hz, 2 H) 7.14-7.21 (m, J=7.58 Hz, 2 H) 7.26-7.31 (m, J=7.45, 7.45 Hz, 1 H) 7.37-7.45 (m, J=7.83, 7.83 Hz, 2 H) 7.66 (bs, 1 H) 7.83 (dd, J=8.72, 2.15 Hz, 1 H).

後処理

  1. customthe reaction mixture was partitioned between 1.0 M HCl (150 mL) and EtOAc (150 mL)
  2. customThe layers were separated
  3. washthe organic phase was washed with saturated NaHCO3, brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe crude product was purified by flash chromatography (0% to 100% EtOAc in hexanes)

出典と根拠

ORDレコード
ord-f797af9a6dd54bbcb04b5416b86c9a92
出典データセット
uspto-grants-2009_09
特許番号
US07592331B2

反応ノート

読み込み中…