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

HRID 1639701노트

반응식

HRID 1639701 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]=[CH:17][C:16]([CH2:19][C:20]#[N:21])=[C:15]([C:22]([F:25])([F:24])[F:23])[CH:14]=1.C[O-].[Na+]>C(O)C>[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[N:3]=[N:2][N:1]([C:4]3[CH:5]=[CH:6][C:7]([O:10][CH3:11])=[CH:8][CH:9]=3)[C:20]=2[NH2:21])=[C:15]([C:22]([F:23])([F:24])[F:25])[CH:14]=1

참가 물질

5

반응물 3

HCID 750041-Azido-4-methoxybenzeneHCID 37027662-(4-Chloro-2-(trifluoromethyl)phenyl)acetonitrileHCID 10942334Sodium Methoxide

생성물 1

HCID 252161575-(4-Chloro-2-trifluoromethyl-phenyl)-3-(4-methoxy-phenyl)-3h-[1,2,3]triazol-4-ylamine수율 84.9%

시약·촉매·용매 1

HCID 702Ethanol용매2회

실험 절차

To a stirred and ice-cooled solution of 1-azido-4-methoxy-benzene (0.500 g, 3.3523 mmol) and 4-chloro-2-(trifluoromethyl)phenylacetonitrile (1.104 g, 5.0284 mmol) in absolute ethanol (15 ml), an ice-cooled solution of sodium methoxide (0.217 g, 4.0228 mmol) in absolute ethanol (8 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 ˜1.25 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 (1.05 g, 83% yield). M.p. 159.2-160.2° C. LC-ESI-HRMS of [M+H]+ shows 369.0712 Da. Calc. 369.072998 Da, dev. −4.9 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 ˜1.25 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-6bddc64f4b5249d89038ea4a40e5976c
출처 데이터셋
uspto-grants-2012_02
특허 번호
US08110588B2

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