1,1'-Carbonyldiimidazole → HCID 20260903, compound

HRID 648057Notes

Reaction equation

HRID 648057 reaction equation
[CH3:1][C:2]1[C:6]2[CH:7]=[C:8]([CH2:11][C:12]3[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=3)[CH:9]=[CH:10][C:5]=2[O:4][C:3]=1[C:18]([OH:20])=O.C(N1C=CN=C1)([N:23]1C=CN=C1)=O>O1CCOCC1>[CH3:1][C:2]1[C:6]2[CH:7]=[C:8]([CH2:11][C:12]3[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=3)[CH:9]=[CH:10][C:5]=2[O:4][C:3]=1[C:18]([NH2:23])=[O:20]

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 20260938HCID 20260938, compound

Product 1

HCID 20260903HCID 20260903, compoundYield 57.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 3-methyl-5-(3-pyridylmethyl)benzofuran-2-carboxylic acid (0.28 g.), carbonyldiimidazole (0.28 g.) and dioxan (5 ml.) was heated on a steam bath for 2 hours and then evaporated. The residue was dissolved in a concentrated solution of ammonia in ethanol (10 ml.), the solution was allowed to stand for 30 minutes and then evaporated. The residue was chromatographed on silica gel. Elution with chloroform first gave a small amount of impurity followed by pure product. Evaporation of the product-containing fractions gave a solid which was crystallized from isopropanol/petrol (b.p. 60°-80°) to give 3-methyl-5-(3-pyridylmethyl)benzofuran-2-carboxamide (0.16 g.), m.p. 175°-177° C.

Workup

  1. temperaturewas heated on a steam bath for 2 hours
  2. customevaporated
  3. dissolutionThe residue was dissolved in a concentrated solution of ammonia in ethanol (10 ml.)
  4. customevaporated
  5. customThe residue was chromatographed on silica gel
  6. washElution with chloroform
  7. customfirst gave a small amount of impurity
  8. customEvaporation of the product-containing fractions
  9. customgave a solid which
  10. customwas crystallized from isopropanol/petrol (b.p. 60°-80°)

Sources & evidence

ORD record
ord-8d4c3c5c48754278bebce0f62740ecd6
Source dataset
uspto-grants-1983_10
Patent number
US04410539

Reaction notes

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