Hydrochloric Acid → HCID 178464594, compound

HRID 55371Notes

Reaction equation

HRID 55371 reaction equation
[C:1]([N:3]=[C:4]([NH:21][CH2:22][CH3:23])[NH:5][CH2:6][CH2:7][CH2:8][NH:9][CH2:10][CH:11]1[CH2:16][CH2:15][C:14]2[CH:17]=[CH:18][CH:19]=[CH:20][C:13]=2[O:12]1)#[N:2].[ClH:24].CC([OH:28])C>CO>[ClH:24].[ClH:24].[O:12]1[C:13]2[CH:20]=[CH:19][CH:18]=[CH:17][C:14]=2[CH2:15][CH2:16][CH:11]1[CH2:10][NH:9][CH2:8][CH2:7][CH2:6][NH:5][C:4]([NH:21][CH2:22][CH3:23])=[N:3][C:1]([NH2:2])=[O:28]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3776IsopropanolHCID 178464582HCID 178464582, compound

Product 1

HCID 178464594HCID 178464594, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 3.1 g (±)-N"-cyano-N-[3-[[(3,4-dihydro-2H-1-benzopyran-2yl)methyl]amino]propyl]-N'-ethylguanidine in a solution of 10 ml hydrochloric acid in 2-propanol and 50 ml methanol was stirred and refluxed for 30 minutes. The solvent was evaporated. The residue was dissolved in water and this mixture was alkalized with aqueous NaOH (10%). This mixture was extracted with CH2Cl2. The organic layer was separated, washed with water, dried (MgSO4), filtered and the solvent was evaporated. The residue was purified by column chromatography over silica gel (eluent: CH2Cl2 / CH3OH/(NH3)90:10). The pure fractions were collected and the solvent was evaporated. The residue was dissolved in 2-propanol and into the hydrochloric acid salt (1:2) with 2-propanol saturated with HCl. The salt was filtered off and recrystallized from 2-propanol. The crystals were filtered off and dried, yielding 2.95g (±)-N-[[[3-[[(3 ,4-dihydro-2H-1-benzopyran-2-yl) methyl]amino]propyl]amino](ethylamino)methylene]urea dihydrochloride; mp. 182.2° C. (interm. 51).

Workup

  1. temperaturerefluxed for 30 minutes
  2. customThe solvent was evaporated
  3. dissolutionThe residue was dissolved in water
  4. extractionThis mixture was extracted with CH2Cl2
  5. customThe organic layer was separated
  6. washwashed with water
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. customthe solvent was evaporated
  10. customThe residue was purified by column chromatography over silica gel (eluent: CH2Cl2 / CH3OH/(NH3)90:10)
  11. customThe pure fractions were collected
  12. customthe solvent was evaporated
  13. dissolutionThe residue was dissolved in 2-propanol and into the hydrochloric acid salt (1:2) with 2-propanol saturated with HCl
  14. filtrationThe salt was filtered off
  15. customrecrystallized from 2-propanol
  16. filtrationThe crystals were filtered off
  17. customdried

Sources & evidence

ORD record
ord-3e0070c145e249ba9b1cd8a1f6787e90
Source dataset
uspto-grants-1997_04
Patent number
US05624952

Reaction notes

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