Methylamine → HCID 20313198, compound

HRID 2420153Notes

Reaction equation

HRID 2420153 reaction equation
[CH2:1]([N:3]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[N:5]2[C:12](=[O:21])[C:13]([C:16]([O:18]CC)=O)=[CH:14][N:15]=[C:4]12)[CH3:2].[CH3:22][NH2:23]>>[CH2:1]([N:3]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[N:5]2[C:12](=[O:21])[C:13]([C:16]([NH:23][CH3:22])=[O:18])=[CH:14][N:15]=[C:4]12)[CH3:2]

Participants

3

Reactant 2

HCID 6329MethylamineHCID 10850693HCID 10850693, compound

Product 1

HCID 20313198HCID 20313198, compoundYield 63%

Procedure

10 g. of 90% pure 10-ethyl-4,10-dihydro-4-oxo-pyrimido[1,2-a]-benzimidazole-3-carboxylic acid, ethyl ester produced in Example 1b are dissolved in 50 ml. of alcohol. After addition of 10 ml. of methylamine, the solution is heated in an autoclave at 100° for 12 hours. After this time, the solvent is distilled off and the crystalline residue is heated with hot acetone. The small amount of isomeric 1-ethyl-1,4-dihydro-N-methyl-4-oxo-pyrimido[1,2-a]benzimidazole-3-carboxamide is insoluble and is filtered off. After addition of water to the mother liquor, the 10-ethyl-4,10-dihydro-N-methyl-4-oxo-pyrimido-[1,2-a]benzimidazole-3-carboxamide crystallizes, yield 63%; m.p. 178°-180° (acetone).

Workup

  1. additionAfter addition of 10 ml
  2. distillationAfter this time, the solvent is distilled off
  3. temperaturethe crystalline residue is heated with hot acetone
  4. filtrationis filtered off
  5. additionAfter addition of water to the mother liquor
  6. customthe 10-ethyl-4,10-dihydro-N-methyl-4-oxo-pyrimido-[1,2-a]benzimidazole-3-carboxamide crystallizes

Sources & evidence

ORD record
ord-42b67626bc314d3e8bd7492f817c6b48
Source dataset
uspto-grants-1978_08
Patent number
US04109091

Reaction notes

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