Benzeneacetonitrile, 4-methoxy- → HCID 25215912, compound

HRID 1639700Notes

Reaction equation

HRID 1639700 reaction equation
[N:1]([C:4]1[C:9]([I:10])=[CH:8][C:7]([Cl:11])=[CH:6][C:5]=1[Cl:12])=[N+:2]=[N-:3].[CH3:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][C:22]#[N:23])=[CH:17][CH:16]=1.C[O-].[Na+]>C(O)C>[Cl:12][C:5]1[CH:6]=[C:7]([Cl:11])[CH:8]=[C:9]([I:10])[C:4]=1[N:1]1[C:22]([NH2:23])=[C:21]([C:18]2[CH:19]=[CH:20][C:15]([O:14][CH3:13])=[CH:16][CH:17]=2)[N:3]=[N:2]1

Participants

5

Reactant 3

HCID 66031Benzeneacetonitrile, 4-methoxy-HCID 10942334Sodium MethoxideHCID 86645069HCID 86645069, compound

Product 1

HCID 25215912HCID 25215912, compoundYield 10%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a stirred and ice-cooled solution of 2-azido-1,5-dichloro-3-iodo-benzene (0.500 g, 1.5928 mmol) and 4-methoxyphenylacetonitrile (0.29 g, 1.9114 mmol) in absolute ethanol (6 ml), an ice-cooled solution of sodium methoxide (0.129 g, 2.3892 mmol) in absolute ethanol (4 ml) is added drop-wise and the mixture is allowed to reach room temperature spontaneously overnight. The resulting reaction mixture is evaporated and the gummy residue (0.740 g, 100% mass balance) is purified by column chromatography over silica gel (60-120 mesh) eluting with 0-15% ethyl acetate in hexane, to obtain the title compound as a brown solid (0.072 g, 10% yield). M.p. 72.5-73.6° C. LC-ESI-HRMS of [M+H]+ shows 460.9425 Da. Calc. 460.943317 Da, dev. −1.8 ppm.

Workup

  1. additionis added drop-wise
  2. customThe resulting reaction mixture
  3. customis evaporated
  4. customthe gummy residue (0.740 g, 100% mass balance) is purified by column chromatography over silica gel (60-120 mesh)
  5. washeluting with 0-15% ethyl acetate in hexane

Sources & evidence

ORD record
ord-846ec064f1c34146b2e670dd4cdc4a81
Source dataset
uspto-grants-2012_02
Patent number
US08110588B2

Reaction notes

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