Thiophenol → 4-Aminomethyl-2-fluoro-benzonitrile

HRID 1246671ノート

反応式

HRID 1246671 の反応式
C1(S)C=CC=CC=1.C(N(CC)CC)C.[N:15]([CH2:18][C:19]1[CH:26]=[CH:25][C:22]([C:23]#[N:24])=[C:21]([F:27])[CH:20]=1)=[N+]=[N-]>C(#N)C>[NH2:15][CH2:18][C:19]1[CH:26]=[CH:25][C:22]([C:23]#[N:24])=[C:21]([F:27])[CH:20]=1

参加物

5

反応物 3

HCID 7969ThiophenolHCID 8471TriethylamineHCID 219046434-Azidomethyl-2-fluorobenzonitrile

生成物 1

HCID 219046524-Aminomethyl-2-fluoro-benzonitrile収率 72.5%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒2 回

実験手順

To a suspension of stannous chloride dihydrate (0.45 g, 2.4 mmol) in 20 mL of acetonitrile under stirring was added thiophenol (1.07 g, 9.7 mmol) and triethylamine (0.726 g, 7.17 mmol). Thereafter was added a solution of 4azidomethyl-2-fluorobenzonitrile (0.279 g, 1.58 mmol; see step (iv) above) in a few mLs of acetonitrile. After 1.5 h, the azide was consumed and the solvent was evaporated. The residue was dissolved in methylene chloride and washed three times with 2M NaOH. The organic phase was extracted twice with 1M HCl. The combined acidic aqueous phase was washed with methylene chloride and then made alkaline with 2M NaOH and extracted three times with methylene chloride. The organic phase was dried (Na2SO4) and evaporated to give 0.172 g (72%) of the desired sub-title compound which could be used without purification.

後処理

  1. customthe azide was consumed
  2. customthe solvent was evaporated
  3. dissolutionThe residue was dissolved in methylene chloride
  4. washwashed three times with 2M NaOH
  5. extractionThe organic phase was extracted twice with 1M HCl
  6. washThe combined acidic aqueous phase was washed with methylene chloride
  7. extractionextracted three times with methylene chloride
  8. dry with materialThe organic phase was dried (Na2SO4)
  9. customevaporated

出典と根拠

ORDレコード
ord-efcafa8cdfca48cabc2ddc205419f93e
出典データセット
uspto-grants-2006_10
特許番号
US07129233B2

反応ノート

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