Benzeneacetonitrile, 4-methoxy- → HCID 25215442, compound

HRID 1639685Notes

Reaction equation

HRID 1639685 reaction equation
[N:1]([C:4]1[CH:9]=[CH:8][C:7]([F:10])=[CH:6][C:5]=1[Cl:11])=[N+:2]=[N-:3].[CH3:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:20][C:21]#[N:22])=[CH:16][CH:15]=1.C[O-].[Na+]>C(O)C.C(OCC)(=O)C>[Cl:11][C:5]1[CH:6]=[C:7]([F:10])[CH:8]=[CH:9][C:4]=1[N:1]1[C:21]([NH2:22])=[C:20]([C:17]2[CH:18]=[CH:19][C:14]([O:13][CH3:12])=[CH:15][CH:16]=2)[N:3]=[N:2]1

Participants

6

Reactant 3

HCID 66031Benzeneacetonitrile, 4-methoxy-HCID 10942334Sodium MethoxideHCID 43154606HCID 43154606, compound

Product 1

HCID 25215442HCID 25215442, compoundYield 34.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To an ice-cooled and stirred mixture of 1-azido-2-chloro-4-fluoro-benzene (0.300 g, 1 eq) and commercial (4-methoxy-phenyl)-acetonitrile (0.309 g, 1.2 eq) in ethanol (5 ml) kept under nitrogen, a solution of sodium methoxide (0.142 g, 1.5 eq) in ethanol (5 ml) is added drop-wise (15 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 (20 ml), washed with water (2×25 ml), dried over MgSO4 and evaporated to dryness. The yellow semisolid residue (˜0.500 g) is purified by flash chromatography using 60-120 mesh silica gel and eluting with 20% ethylacetate in hexane, to afford the title compound as a white solid (0.190 g, 34% yield). M.p. 136.3-141.2° C.

Workup

  1. additionAfter the addition
  2. customto reach room temperature
  3. stirringstirring
  4. customThe resulting reaction mixture
  5. washwashed with water (2×25 ml)
  6. dry with materialdried over MgSO4
  7. customevaporated to dryness
  8. customThe yellow semisolid residue (˜0.500 g) is purified by flash chromatography
  9. washeluting with 20% ethylacetate in hexane

Sources & evidence

ORD record
ord-a617c825dc354df38a0e66c874090241
Source dataset
uspto-grants-2012_02
Patent number
US08110588B2

Reaction notes

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