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

HRID 1639701Notes

Reaction equation

HRID 1639701 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-6bddc64f4b5249d89038ea4a40e5976c
Source dataset
uspto-grants-2012_02
Patent number
US08110588B2

Reaction notes

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