Hydrochloric Acid → HCID 20393015, compound

HRID 1862991Notes

Reaction equation

HRID 1862991 reaction equation
[NH2:1][C:2]1[N:6]([CH2:7][CH2:8][C:9]([OH:11])=[O:10])[C:5]2[CH:12]=[CH:13][C:14]([C:16](=[O:23])[C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[CH:15][C:4]=2[N:3]=1.Cl.[C:25](=O)(O)[O-].[Na+]>CO>[NH2:1][C:2]1[N:6]([CH2:7][CH2:8][C:9]([O:11][CH3:25])=[O:10])[C:5]2[CH:12]=[CH:13][C:14]([C:16](=[O:23])[C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[CH:15][C:4]=2[N:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 20393004HCID 20393004, compound

Product 1

HCID 20393015HCID 20393015, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of 3-(2-amino-5-benzoylbenzimidazol-1-yl)-propionic acid (6.1 g.) in methanol (30 ml.) was treated with a saturated solution (30 ml.) of hydrogen chloride in methanol. The mixture was left at room temperature for 16 hours and then evaporated. The residue was dissolved in water. The solution obtained was adjusted to pH 8.5 with aqueous sodium bicarbonate solution and then extracted with ethyl acetate (3×50 ml.). The extracts were dried (MgSO4) and evaporated to give methyl 3-(2-amino-5-benzoylbenzimidazol-1-yl)propionate as an oil. This oil was dissolved in methanol (60 ml.) and the solution heated at reflux for 5 hours. The solid which precipitated was collected and washed successively with methanol, acetone and then ether to give 8-benzoyl-3,4-dihydropyrimido[1,2-a]-benzimidazol-2(1H)-one (3.4 g.), m.p. 323°-330° C., microanalysis, C17H13N3O2 requires: C, 70.1; H, 4.5; N, 14.4% found: C, 69.9; H, 4.4; N, 14.0%.

Workup

  1. customevaporated
  2. dissolutionThe residue was dissolved in water
  3. customThe solution obtained
  4. extractionextracted with ethyl acetate (3×50 ml.)
  5. dry with materialThe extracts were dried (MgSO4)
  6. customevaporated

Sources & evidence

ORD record
ord-afc5459cf5af4550969b9ac40a99c88d
Source dataset
uspto-grants-1979_09
Patent number
US04167569

Reaction notes

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