Benzeneacetonitrile, 4-methoxy- → HCID 25154238, compound

HRID 1639683Notes

Reaction equation

HRID 1639683 reaction equation
[N:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]([F:13])([F:12])[F:11])=[CH:6][C:5]=1[Cl:14])=[N+:2]=[N-:3].[CH3:15][O:16][C:17]1[CH:22]=[CH:21][C:20]([CH2:23][C:24]#[N:25])=[CH:19][CH:18]=1.C[O-].[Na+]>C(O)C.C(OCC)(=O)C>[Cl:14][C:5]1[CH:6]=[C:7]([C:10]([F:12])([F:13])[F:11])[CH:8]=[CH:9][C:4]=1[N:1]1[C:24]([NH2:25])=[C:23]([C:20]2[CH:21]=[CH:22][C:17]([O:16][CH3:15])=[CH:18][CH:19]=2)[N:3]=[N:2]1

Participants

6

Reactant 3

HCID 66031Benzeneacetonitrile, 4-methoxy-HCID 10942334Sodium MethoxideHCID 63668480HCID 63668480, compound

Product 1

HCID 25154238HCID 25154238, compoundYield 30%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To an ice-cooled and stirred mixture of 1-azido-2-chloro-4-trifluoromethyl-benzene (1.00 g, 1 eq) and commercial (4-methoxy-phenyl)-acetonitrile (0.797 g, 1.2 eq) in ethanol (10 ml) kept under nitrogen, a solution of sodium methoxide (0.366 g, 1.5 eq) in ethanol (10 ml) is added drop-wise (20 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 solid residue (1.20 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 (0.324 g, 30% yield). M.p. 130.0-130.7° 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 solid residue (1.20 g) is purified by flash chromatography
  9. washeluting with 15% ethylacetate in hexane

Sources & evidence

ORD record
ord-0a47f1852be64e6d8e9b7e60f349bfe4
Source dataset
uspto-grants-2012_02
Patent number
US08110588B2

Reaction notes

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