Triphenylphosphine → 4-(Aminomethyl)-3-chlorobenzonitrile

HRID 896246

反応式

HRID 896246 の反応式
[Cl:1][C:2]1[CH:11]=[C:10]([C:12]#[N:13])[CH:9]=[CH:8][C:3]=1[CH2:4][N:5]=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[OH-].[Na+]>C1COCC1.O>[Cl:1][C:2]1[CH:11]=[C:10]([C:12]#[N:13])[CH:9]=[CH:8][C:3]=1[CH2:4][NH2:5]

参加物

5

反応物 3

HCID 11776TriphenylphosphineHCID 14798Sodium HydroxideHCID 223499744-Azidomethyl-3-chlorobenzonitrile

生成物 1

HCID 40897884-(Aminomethyl)-3-chlorobenzonitrile収率 90%

試薬・触媒・溶媒 1

HCID 21881883Oxolane--water (1/1)溶媒

実験手順

To a solution of 2-choro-4-cyanobenzyl azide (5.8 g, 30.1 mmol) in THF/H2O (3:1), was added triphenyl phosphine (12.3 g, 46.7 mmol). The reaction was stirred at room temperature overnight, then neutralized with 1N sodium hydroxide, extracted with ethyl acetate (150 ml×3). The organic layer was dried over sodium sulfate, and then solvent was removed in vacuo. The product was purified by silica-gel chromatography column with methanol/ammonia hydroxide/ethyl acetate (20:1:69) to give 4.5 g (90%) of 2-chloro-4-cyanobenzylamine. NMR (CDCl3): δ 4.0 (s, 2H, CH2), 7.58 (d, 2H, HAr), 7.62 (s, 1H, HAr)

後処理

  1. extractionextracted with ethyl acetate (150 ml×3)
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. customsolvent was removed in vacuo
  4. customThe product was purified by silica-gel chromatography column with methanol/ammonia hydroxide/ethyl acetate (20:1:69)

出典と根拠

ORDレコード
ord-e48da4a9ef5343e9957067963b6369f3
出典データセット
uspto-grants-2005_07
特許番号
US06919347B2

関連ノート

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