1,1'-Carbonyldiimidazole → Methyl 3-(4-methoxyphenyl)methylthiopyridine-4-carboxylate

HRID 1200011Notes

Reaction equation

HRID 1200011 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]2[CH:11]=[N:12][CH:13]=[CH:14][C:15]=2[C:16]([OH:18])=[S:17])=[CH:5][CH:4]=1.[C:19](N1C=CN=C1)(N1C=CN=C1)=O>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:9][C:10]2[CH:11]=[N:12][CH:13]=[CH:14][C:15]=2[C:16]([O:18][CH3:19])=[S:17])=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 178489829HCID 178489829, compound

Product 1

HCID 86742397Methyl 3-(4-methoxyphenyl)methylthiopyridine-4-carboxylateYield 104.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4.9 g (17.8 mmol) of 3-(4-methoxyphenyl)methylthiopyridine-4-carboxylic acid and 4.9 g (30 mmol) of carbonyldiimidazole in 50 mL of dry N,N-dimethylformamide was stirred at 0° C. for 10 minutes and then allowed to warm to room temperature. After 2 hours the solution was cooled to 10° C. and quenched with 20 mL of methanol. The mixture was stirred for 2 hours and then the solvent was concentrated. The residue was partitioned between ether and water and the aqueous layer was extracted with three portions of ether. The ether extracts were dried (MgSO4) and concentrated to afford 5.1 g (93%) of a crystalline solid, m.p. 99°-100° C.

Workup

  1. temperatureAfter 2 hours the solution was cooled to 10° C.
  2. customquenched with 20 mL of methanol
  3. concentrationthe solvent was concentrated
  4. customThe residue was partitioned between ether and water
  5. extractionthe aqueous layer was extracted with three portions of ether
  6. dry with materialThe ether extracts were dried (MgSO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-c573a09496384369922b9d254570908c
Source dataset
uspto-grants-1990_02
Patent number
US04904672

Reaction notes

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