Tosylmethyl isocyanide → HCID 66759906, compound

HRID 564234Notes

Reaction equation

HRID 564234 reaction equation
[CH:1]([C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9]C)=[O:8])=[CH:5][N:4]=1)=[O:2].C[O-].[Na+].S([CH2:26][N+:27]#[C-:28])(C1C=CC(C)=CC=1)(=O)=O>CO>[O:2]1[C:1]([C:3]2[CH:12]=[CH:11][C:6]([C:7]([OH:9])=[O:8])=[CH:5][N:4]=2)=[CH:28][N:27]=[CH:26]1

Participants

5

Reactant 3

HCID 161915Tosylmethyl isocyanideHCID 586269Methyl 6-formylpyridine-3-carboxylateHCID 10942334Sodium Methoxide

Product 1

HCID 66759906HCID 66759906, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a suspension of methyl 6-formylnicotinate (60 mg, 0.363 mmol) in methanol (3 mL) was added sodium methoxide in methanol (0.5M, 2.91 mL, 1.45 mmol). Tosylmethyl isocyanide (85 mg, 0.436 mmol) was added to the reaction and the mixture was heated at reflux overnight. After cooling, the reaction mixture was concentrated. The residue was treated with 5% citric acid/50% brine (1:1) and extracted with ethyl acetate. The suspension was filtered, washed with water, and dried under vacuum to provide the title compound. MS (DCI/NH3) m/z: 191.0 (M+1)+.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux overnight
  3. temperatureAfter cooling
  4. concentrationthe reaction mixture was concentrated
  5. additionThe residue was treated with 5% citric acid/50% brine (1:1)
  6. extractionextracted with ethyl acetate
  7. filtrationThe suspension was filtered
  8. washwashed with water
  9. customdried under vacuum

Sources & evidence

ORD record
ord-278d018e625844f4a5b94332ddaee80d
Source dataset
uspto-grants-2011_11
Patent number
US08067613B2

Reaction notes

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