Hydrochloric Acid → HCID 178431756, compound

HRID 895493Notes

Reaction equation

HRID 895493 reaction equation
[O-]CC.[Na+].Cl.[C:6]([NH2:14])(=[NH:13])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C([O:17][C:18](=O)[CH:19]([CH3:25])[C:20](OCC)=[O:21])C.Cl>C(O)C>[CH3:25][C:19]1[C:20]([OH:21])=[N:13][C:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:14][C:18]=1[OH:17]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11857Diethyl methylmalonateHCID 80289Benzamidine, hydrochlorideHCID 2723922Sodium ethoxide

Product 1

HCID 178431756HCID 178431756, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
40 °C

Procedure

To ethanol (180 ml) was added sodium ethoxide solution (38 ml of a 21% wt solution in ethanol), benzamidine hydrochloride (5.0 g) and diethylmethylmalonate (4.91 ml). The suspension was stirred at 40° C. in an inert atmosphere for 22 hrs after which time it was cooled to 5° C. (ice bath) and treated dropwise with concentrated hydrochloric acid to a pH of 2.5. The resulting pink suspension was filtered and washed with excess water. Purification by recrystallisation from boiling acetic acid (300 ml) afforded the title compound (4.22 g) after filtration and washing with ethanol (20 ml) and diethyl ether (20 ml).

Workup

  1. temperaturewas cooled to 5° C. (ice bath)
  2. filtrationThe resulting pink suspension was filtered
  3. washwashed with excess water
  4. customPurification
  5. customby recrystallisation

Sources & evidence

ORD record
ord-78ed13cfa54c453eb9a635591e686b97
Source dataset
uspto-grants-2005_07
Patent number
US06916804B2

Reaction notes

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