Thionyl Chloride → HCID 20313192, compound

HRID 2420154Notes

Reaction equation

HRID 2420154 reaction equation
[CH2:1]([N:3]1[C:8]2=[N:9][C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N:7]2[C:6](=[O:16])[C:5]([C:17](O)=[O:18])=[CH:4]1)[CH3:2].S(Cl)(Cl)=O>>[CH2:1]([N:3]1[C:8]2=[N:9][C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N:7]2[C:6](=[O:16])[C:5]([C:17]([NH:7][C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:10]=2)=[O:18])=[CH:4]1)[CH3:2]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 20313190HCID 20313190, compound

Product 1

HCID 20313192HCID 20313192, compoundYield 73%

Procedure

0.05 mol. of 1-ethyl-1,4-dihydro-4-oxo-pyrimido-[1,2-a]benzimidazole-3-carboxylic acid is refluxed with stirring in 100 ml. of thionyl chloride. After this time, the chlorinating agent is removed by distillation, the remaining acid chloride is treated with 50 ml. of toluene and again evaporated to dryness. After addition of 100 ml. of toluene, 0.1 mol. of aniline are added and the solution is stirred overnight. The solvent is distilled off and the residue treated with water and filtered. The product 1-ethyl-1,4-dihydro-4-oxo-N-phenyl-pyrimido[1,2-a]benzimidazole-3-carboxamide, is recrystallized from DMF, yield 73%; m.p. 268°-270°.

Workup

  1. customAfter this time, the chlorinating agent is removed by distillation
  2. additionthe remaining acid chloride is treated with 50 ml
  3. customof toluene and again evaporated to dryness
  4. additionAfter addition of 100 ml
  5. additionof aniline are added
  6. stirringthe solution is stirred overnight
  7. distillationThe solvent is distilled off
  8. additionthe residue treated with water
  9. filtrationfiltered
  10. customThe product 1-ethyl-1,4-dihydro-4-oxo-N-phenyl-pyrimido[1,2-a]benzimidazole-3-carboxamide, is recrystallized from DMF, yield 73%

Sources & evidence

ORD record
ord-dfb40f5a080d4735abcaaf2e2816148a
Source dataset
uspto-grants-1978_08
Patent number
US04109091

Reaction notes

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