Hydrochloric Acid → HCID 178478777, compound

HRID 1862840Notes

Reaction equation

HRID 1862840 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]1[N:8]=[CH:7][NH:6][CH:5]=1.C1(C)C=CC=C([O:15][C:16](=[NH:20])[NH:17][C:18]#[N:19])C=1.[ClH:22]>C(O)(C)C>[ClH:22].[ClH:22].[NH:6]1[CH:5]=[C:4]([CH2:3][CH2:2][NH:1][C:18]([NH:17][C:16]([NH2:20])=[O:15])=[NH:19])[N:8]=[CH:7]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 178419017HCID 178419017, compoundHCID 178425733HCID 178425733, compound

Product 1

HCID 178478777HCID 178478777, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent2×

Procedure

47.5 g. histamine (0.401 mole) and 71.66 g. (0.409 mole) O-m-tolyl-N-cyanoisourea are combined in 500 ml. of isopropanol. The mixture is then heated for 10 minutes to reflux, refluxed for one hour, and the reaction mixture is stripped to an oil. The oil is taken up in 2 l. of isopropanol and 102 ml. conc. HCl, heated 25 minutes to reflux, refluxed for 35 minutes, cooled slowly, then with ice. The mixture is filtered to obtain 1-[2-(4-imidazolyl)ethylamidino]urea dihydrochloride as a crude product. This is recrystallized from MeOH/CH3CN to obtain 1-[2-(4-imidazolyl)ethylamidino]urea dihydrochloride with a m.p. of 180.5°-181.5° C.

Workup

  1. temperatureThe mixture is then heated for 10 minutes
  2. temperatureto reflux
  3. temperaturerefluxed for one hour
  4. temperatureto reflux
  5. temperaturerefluxed for 35 minutes
  6. temperaturecooled slowly
  7. filtrationThe mixture is filtered

Sources & evidence

ORD record
ord-ed8546f75d9d4b9082df480bcbd9453e
Source dataset
uspto-grants-1979_09
Patent number
US04166860

Reaction notes

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