Hydrochloric Acid → HCID 86734412, compound

HRID 1415104Notes

Reaction equation

HRID 1415104 reaction equation
[Cl:1]([O-:5])(=[O:4])(=[O:3])=[O:2].C(OC([C:11]1[CH:12]([CH3:25])[CH2:13][CH2:14][N:15]2[C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=3[NH+:17]([CH3:24])[C:16]=12)=O)C.Cl>CC(N(C)C)=O.CCOCC>[Cl:1]([O-:5])(=[O:4])(=[O:3])=[O:2].[CH3:25][CH:12]1[CH2:13][CH2:14][N:15]2[C:16]([NH+:17]([CH3:24])[C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=32)=[CH:11]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 86734410HCID 86734410, compound

Product 1

HCID 86734412HCID 86734412, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 31374DimethylacetamideSolvent

Procedure

4-Ethoxycarbonyl-1,2-dihydro-3,5-dimethyl-5H-pyrido[1,2-a]benzimidazolium perchlorate (7.92g; 0.0213 mole) is boiled with stirring for 40 minutes in dimethylacetamide (50ml) containing concentrated HCl (3ml). During the reaction approximately half of the solution is allowed to boil away. The cooled reaction mixture is stirred overnight in a liter of ether. The ether is decanted and the residue is dissolved in hot water (300 ml) and filtered. Upon cooling to room temperature some gummy material separates on the walls of the flask. The clear solution is decanted, cooled with an ice bath, and treated with 30g of sodium perchlorate. The crude product which separates is filtered, washed with a little water then ether, and recrystallized from ethanol to give 3.28g (51.6%); m.p. 206°-210° d.

Workup

  1. customDuring the reaction approximately half of the solution
  2. customThe cooled reaction mixture
  3. customThe ether is decanted
  4. dissolutionthe residue is dissolved in hot water (300 ml)
  5. filtrationfiltered
  6. customThe clear solution is decanted
  7. temperaturecooled with an ice bath
  8. additiontreated with 30g of sodium perchlorate
  9. filtrationThe crude product which separates is filtered
  10. washwashed with a little water
  11. customether, and recrystallized from ethanol
  12. customto give 3.28g (51.6%)

Sources & evidence

ORD record
ord-d3e54b5932434621a1610e84f26cefa1
Source dataset
uspto-grants-1977_01
Patent number
US04003750

Reaction notes

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