Guanidine Hydrochloride → HCID 178513066, compound

HRID 1792796Notes

Reaction equation

HRID 1792796 reaction equation
Cl.[NH2:2][C:3]([NH2:5])=[NH:4].C[O-].[Na+].Cl.Cl[C:11]([C:13]1[CH:17]=[CH:16][N:15]([C:18]2[CH:27]=[CH:26][CH:25]=[C:24]3[C:19]=2[CH:20]=[CH:21][CH:22]=[N:23]3)[CH:14]=1)=[O:12]>CO.O1CCCC1.ClCCl>[NH:4]([C:11]([C:13]1[CH:17]=[CH:16][N:15]([C:18]2[CH:27]=[CH:26][CH:25]=[C:24]3[C:19]=2[CH:20]=[CH:21][CH:22]=[N:23]3)[CH:14]=1)=[O:12])[C:3]([NH2:5])=[NH:2]

Participants

6

Reactant 3

HCID 5742Guanidine HydrochlorideHCID 10942334Sodium MethoxideHCID 22024994HCID 22024994, compound

Product 1

HCID 178513066HCID 178513066, compoundYield 31.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 21919333Tetrahydrofurane dichloromethaneSolvent

Conditions

Temperature
22 °C

Procedure

0.9 g (9.42 mmol) of guanidine hydrochloride is added to a solution of 0.51 g (9.44 mmol) of sodium methoxide in 15 mL of methanol at a temperature in the region of 22° C. under an argon atmosphere. After stirring at a temperature in the region of 22° C. for 2 hours, the solvent is evaporated off under reduced pressure (2.7 kPa). The residue, placed under an argon atmosphere, is taken up in 20 mL of a tetrahydrofuran/dichloromethane (1/1 by volume) mixture and then 0.55 g (1.88 mmol) of 3-chlorocarbonyl-1-(quinol-5-yl)-1H-pyrrole hydrochloride, dissolved in 5 mL of the same tetrahydrofuran/dichloromethane mixture, is added thereto. After stirring at a temperature in the region of 22° C. for 15 hours, the reaction mixture is concentrated to dryness under reduced pressure (2.7 kPa). The residue is triturated with water, filtered and taken up under hot conditions in 7 mL of ethanol. The insoluble material is then filtered off and discarded, and the filtrate is cooled to a temperature in the region of 22° C. The crystals formed are filtered off and dried under vacuum (2.7 kPa), to give 0.165 g of 3-guanidinocarbonyl-1-(quinol-5-yl)-1H-pyrrole in the form of a white solid melting at 260° C. Mass spectrum (EI): m/e 279 (M+.), m/e 221.

Workup

  1. customthe solvent is evaporated off under reduced pressure (2.7 kPa)
  2. additionis added
  3. stirringAfter stirring at a temperature in the region of 22° C. for 15 hours
  4. concentrationthe reaction mixture is concentrated to dryness under reduced pressure (2.7 kPa)
  5. customThe residue is triturated with water
  6. filtrationfiltered
  7. filtrationThe insoluble material is then filtered off
  8. temperaturethe filtrate is cooled to a temperature in the region of 22° C
  9. customThe crystals formed
  10. filtrationare filtered off
  11. customdried under vacuum (2.7 kPa)

Sources & evidence

ORD record
ord-3300df1e364043fc82c01144ac6b645b
Source dataset
uspto-grants-2006_07
Patent number
US07078414B2

Reaction notes

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