Methanol → HCID 21833796, compound

HRID 1741078Notes

Reaction equation

HRID 1741078 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([CH:6]=[CH:7][NH2:8])=[CH:4][C:3]=1[CH3:11].CO.S([CH2:24][N+:25]#[C-:26])(C1C=CC(C)=CC=1)(=O)=O.C(=O)([O-])[O-].[K+].[K+]>COCCOC>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]2[N:25]([CH3:26])[CH:24]=[N:8][CH:7]=2)=[CH:4][C:3]=1[CH3:11]

Participants

6

Reactant 4

HCID 887MethanolHCID 11430Potassium CarbonateHCID 161915Tosylmethyl isocyanideHCID 70197996HCID 70197996, compound

Product 1

HCID 21833796HCID 21833796, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

(4-Bromo-3-methylbenzylidene)methylamine (D91, 2.15 g, 10.1 mmol) was dissolved in dry DME (30 ml) and methanol (70 ml) containing tosylmethylisocyanide (3.0 g; 15.4 mmol) and this solution was treated with potassium carbonate (2.8 g, 20.3 mmol). The whole was heated at reflux for 48 hours, cooled and evaporated in vacuo. The residue was partitioned between brine and chloroform (3 times), and the organics combined and dried over Na2SO4. The organics were filtered and evaporated in vacuo then the residue purified by flash silica gel chromatography (with chloroform as eluant) to yield the title compound as an orange gum (1.52 g, 60%).

Workup

  1. temperatureThe whole was heated
  2. temperatureat reflux for 48 hours
  3. temperaturecooled
  4. customevaporated in vacuo
  5. customThe residue was partitioned between brine and chloroform (3 times)
  6. dry with materialdried over Na2SO4
  7. filtrationThe organics were filtered
  8. customevaporated in vacuo
  9. customthe residue purified by flash silica gel chromatography (with chloroform as eluant)

Sources & evidence

ORD record
ord-32bb9132b80a42ce8dee2054b38119d1
Source dataset
uspto-grants-1999_10
Patent number
US05972951

Reaction notes

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