1,1'-Carbonyldiimidazole → HCID 53664452, compound

HRID 1200005Notes

Reaction equation

HRID 1200005 reaction equation
[C:1]1([CH2:7][C:8]2[N:16]=[CH:15][CH:14]=[CH:13][C:9]=2[C:10]([OH:12])=[S:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:17](N1C=CN=C1)(N1C=CN=C1)=O.C[O-].[Na+]>CN(C)C=O.CO>[C:1]1([CH2:7][C:8]2[N:16]=[CH:15][CH:14]=[CH:13][C:9]=2[C:10]([O:12][CH3:17])=[S:11])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 10942334Sodium MethoxideHCID 178526140HCID 178526140, compound

Product 1

HCID 53664452HCID 53664452, compoundYield 95.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 18.3 g (75 mmol) of 2-phenylmethylthionicotinic acid and 16.2 g (100 mmol) of carbonyldiimidazole in 250 mL of dry dimethylformamide was stirred at room temperature for 2 hours. The solution was cooled to 0° and 25 mL of 4M sodium methoxide in methanol was added. After warming to room temperature the solution was partitioned between ether and water and the aqueous layer was washed with two portions of ether. The ether extracts were washed with brine, dried over MgSO4, and concentrated. The residue was crystallized from ether-hexane to afford 17.4 g (89%) of fine white needles, which was used in the next step without further purification.

Workup

  1. temperatureThe solution was cooled to 0°
  2. customwas partitioned between ether and water
  3. washthe aqueous layer was washed with two portions of ether
  4. washThe ether extracts were washed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customThe residue was crystallized from ether-hexane

Sources & evidence

ORD record
ord-b73a4abfda25458097407d0b6c1b67cf
Source dataset
uspto-grants-1990_02
Patent number
US04904672

Reaction notes

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