2,4-Difluorophenylacetonitrile → 5-(2,4-Difluoro-phenyl)-3-(4-methoxy-phenyl)-3H-[1,2,3]triazol-4-ylamine

HRID 1639702노트

반응식

HRID 1639702 반응식
[N:1]([C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][CH:5]=1)=[N+:2]=[N-:3].[F:12][C:13]1[CH:18]=[C:17]([F:19])[CH:16]=[CH:15][C:14]=1[CH2:20][C:21]#[N:22].C[O-].[Na+]>C(O)C>[F:12][C:13]1[CH:18]=[C:17]([F:19])[CH:16]=[CH:15][C:14]=1[C:20]1[N:3]=[N:2][N:1]([C:4]2[CH:5]=[CH:6][C:7]([O:10][CH3:11])=[CH:8][CH:9]=2)[C:21]=1[NH2:22]

참가 물질

5

반응물 3

HCID 695652,4-DifluorophenylacetonitrileHCID 750041-Azido-4-methoxybenzeneHCID 10942334Sodium Methoxide

생성물 1

HCID 252161585-(2,4-Difluoro-phenyl)-3-(4-methoxy-phenyl)-3H-[1,2,3]triazol-4-ylamine수율 54.3%

시약·촉매·용매 1

HCID 702Ethanol용매2회

실험 절차

To a stirred and ice-cooled solution of 1-azido-4-methoxy-benzene (1.000 g, 6.7046 mmol) and 2,4-difluoro phenyl acetonitrile (1.27 g, 8.0455 mmol) in absolute ethanol (20 ml), an ice-cooled solution of sodium methoxide (0.543 g, 10.0569 mmol) in absolute ethanol (10 ml) is added drop-wise. The resulting reaction mixture is evaporated and the residue is dissolved in methylene chloride and washed with water, brine, dried over MgSO4, filtered and evaporated to afford ˜2 g of crude material as brownish solid. This material is purified by crystallization from methylene chloride and petroleum ether, to obtain the title compound as brown solid (1.10 g, 48% yield). M.p. 152-156.5° C. LC-ESI-HRMS of [M+H]+ shows 303.1046 Da. Calc. 303.105742 Da, dev. −3.8 ppm.

후처리

  1. additionis added drop-wise
  2. customThe resulting reaction mixture
  3. customis evaporated
  4. dissolutionthe residue is dissolved in methylene chloride
  5. washwashed with water, brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customevaporated
  9. customto afford ˜2 g of crude material as brownish solid
  10. customThis material is purified by crystallization from methylene chloride and petroleum ether

출처 및 근거

ORD 기록
ord-96c442f6226c4b438ae3ff455662c903
출처 데이터셋
uspto-grants-2012_02
특허 번호
US08110588B2

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