Ethyl Acetate → tert-butyl N-[4-(cyanomethyl)-2-methylphenyl]carbamate

HRID 1861962ノート

反応式

HRID 1861962 の反応式
[C:1]([O:5][C:6](=[O:17])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14]Br)=[CH:10][C:9]=1[CH3:16])([CH3:4])([CH3:3])[CH3:2].[C-:18]#[N:19].[Na+].C(OCC)(=O)C>CS(C)=O>[C:1]([O:5][C:6](=[O:17])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][C:18]#[N:19])=[CH:10][C:9]=1[CH3:16])([CH3:4])([CH3:3])[CH3:2]

参加物

5

反応物 3

HCID 8857Ethyl AcetateHCID 8929Sodium CyanideHCID 22981310HCID 22981310、化合物

生成物 1

HCID 53943733tert-butyl N-[4-(cyanomethyl)-2-methylphenyl]carbamate収率 61.1%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
50 °C

実験手順

The compound (155.1 mg) obtained in Example 519 was dissolved in dimethyl sulfoxide (5 ml). To the solution, sodium cyanide (127 mg) was added and the mixture was heated at 50° C. under stirring for 10 min. To the resulting reaction mixture, ethyl acetate was added and the organic layer was washed with water twice, dried with anhydrous sodium sulfate and the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent, n-hexane:ethyl acetate=3:1) to give 77.7 mg of the titled compound (yield, 61%).

後処理

  1. additionwas added
  2. washthe organic layer was washed with water twice
  3. dry with materialdried with anhydrous sodium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography (eluent, n-hexane:ethyl acetate=3:1)

出典と根拠

ORDレコード
ord-0e2092eb16e741319a97bb91a82ba399
出典データセット
uspto-grants-2003_03
特許番号
US06534546B1

反応ノート

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