1-Azido-4-methoxybenzene → 5-(2-Chloro-4-fluoro-phenyl)-3-(4-methoxy-phenyl)-3h-[1,2,3]triazol-4-ylamine

HRID 1639703노트

반응식

HRID 1639703 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].[Cl: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>[Cl: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 750041-Azido-4-methoxybenzeneHCID 27250632-Chloro-4-fluorophenylacetonitrileHCID 10942334Sodium Methoxide

생성물 1

HCID 252161595-(2-Chloro-4-fluoro-phenyl)-3-(4-methoxy-phenyl)-3h-[1,2,3]triazol-4-ylamine수율 66.4%

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-chloro-4-fluoro phenyl acetonitrile (1.758 g, 10.0569 mmol) in absolute ethanol (15 ml), an ice-cooled solution of sodium methoxide (0.435 g, 8.0455 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 ˜2.2 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 yellowish solid (1.42 g, 66% yield). M.p. 175-176.8° C. LC-ESI-HRMS of [M+H]+ shows 319.0745 Da. Calc. 319.076192 Da, dev. −5.3 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 ˜2.2 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-9692c5b4d7fd439bb4404a2ba194e126
출처 데이터셋
uspto-grants-2012_02
특허 번호
US08110588B2

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