Acetic Anhydride → HCID 14459117, compound

HRID 359694Notes

Reaction equation

HRID 359694 reaction equation
C(O[C:5](=[O:7])C)(=O)C.[CH3:8][C:9]1[CH:14]=[C:13]([CH3:15])[N:12]=[C:11]([N:16]2[CH:20]=[CH:19][N:18]=[C:17]2[S:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[NH2:29])[CH:10]=1>C(O)=O>[CH3:8][C:9]1[CH:14]=[C:13]([CH3:15])[N:12]=[C:11]([N:16]2[CH:20]=[CH:19][N:18]=[C:17]2[S:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[NH:29][CH:5]=[O:7])[CH:10]=1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 14459112HCID 14459112, compound

Product 1

HCID 14459117HCID 14459117, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent2×

Conditions

Temperature
60 °C

Procedure

1.4 g of acetic acid anhydride are added to 2.5 ml of formic acid, and the mixture is stirred at 60° C. for 30 minutes. The reaction solution is cooled in an ice bath, a solution of 1.07 g of 1-(4,6-dimethyl-2-pyridyl)-2-(2-aminobenzylthio)imidazole in 4 ml of formic acid is added thereto, and the mixture is stirred at room temperature for 1 hour. After the reaction, the solvent is distilled off. Water is added to the residue, and the aqueous mixture is made alkaline with potassium carbonate. The mixture is then extracted with ethyl acetate, dried and evaporated to remove the solvent. The residue is purified by silica gel column chromatography (solvent; ethyl acetate:n-hexane=1:1). The crude crystals obtained above are recrystallized from a mixture of ethyl acetate and n-hexane, whereby 0.64 g of 1-(4,6-dimethyl-2-pyridyl)-2-(2-formylaminobenzylthio)imidazole is obtained.

Workup

  1. temperatureThe reaction solution is cooled in an ice bath
  2. stirringthe mixture is stirred at room temperature for 1 hour
  3. customAfter the reaction
  4. distillationthe solvent is distilled off
  5. additionWater is added to the residue
  6. extractionThe mixture is then extracted with ethyl acetate
  7. customdried
  8. customevaporated
  9. customto remove the solvent
  10. customThe residue is purified by silica gel column chromatography (solvent; ethyl acetate:n-hexane=1:1)
  11. customThe crude crystals obtained above
  12. customare recrystallized from a mixture of ethyl acetate and n-hexane

Sources & evidence

ORD record
ord-8cca76ebc1754a7f88f823f18489db27
Source dataset
uspto-grants-1991_03
Patent number
US05002945

Reaction notes

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