1-Azido-4-methoxybenzene → 5-(2,4-Dichlorophenyl)-3-(4-methoxyphenyl)triazol-4-amine

HRID 1639686Notes

Reaction equation

HRID 1639686 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]=[C:17]([Cl:19])[CH:16]=[CH:15][C:14]=1[CH2:20][C:21]#[N:22].C[O-].[Na+]>C(O)C.C(OCC)(=O)C>[Cl:12][C:13]1[CH:18]=[C:17]([Cl: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]

Participants

6

Reactant 3

HCID 750041-Azido-4-methoxybenzeneHCID 805662,4-DichlorophenylacetonitrileHCID 10942334Sodium Methoxide

Product 1

HCID 252154435-(2,4-Dichlorophenyl)-3-(4-methoxyphenyl)triazol-4-amineYield 25.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To an ice-cooled and stirred mixture of 1-azido-4-methoxy-benzene (0.750 g, 1 eq) and commercial (2,4-dichloro-phenyl)-acetonitrile (1.12 g, 1.2 eq) in ethanol (10 ml) kept under nitrogen, a solution of sodium methoxide (0.408 g, 1.5 eq) in ethanol (10 ml) is added drop-wise (25 min). After the addition, the reaction mixture is allowed to reach room temperature spontaneously and stirring is then continued overnight at room temperature. The resulting reaction mixture is diluted with ethyl acetate (40 ml), washed with water (2×50 ml), dried over MgSO4 and evaporated to dryness. The yellow semisolid residue (0.842 g) is purified by flash chromatography using 60-120 mesh silica gel and eluting with 15% ethylacetate in hexane, to afford the title compound as a white solid (0.428 g, 24% yield). M.p. 154.6-163.9° C.

Workup

  1. additionAfter the addition
  2. customto reach room temperature
  3. stirringstirring
  4. customThe resulting reaction mixture
  5. washwashed with water (2×50 ml)
  6. dry with materialdried over MgSO4
  7. customevaporated to dryness
  8. customThe yellow semisolid residue (0.842 g) is purified by flash chromatography
  9. washeluting with 15% ethylacetate in hexane

Sources & evidence

ORD record
ord-67709d0011cb4a1bbcc068801243af2c
Source dataset
uspto-grants-2012_02
Patent number
US08110588B2

Reaction notes

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