Thiophenol → 4-Aminomethyl-2-fluoro-benzonitrile

HRID 1246671

반응식

HRID 1246671 반응식
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

참가 물질

5

반응물 3

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

생성물 1

HCID 219046524-Aminomethyl-2-fluoro-benzonitrile수율 72.5%

시약·촉매·용매 1

HCID 6342Acetonitrile용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-efcafa8cdfca48cabc2ddc205419f93e
출처 데이터셋
uspto-grants-2006_10
특허 번호
US07129233B2

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