Hydrochloric Acid → Bis-guanidine dihydrochloride

HRID 2424858Notes

Reaction equation

HRID 2424858 reaction equation
C([NH:8][C:9](=[N:11]C(OC(C)(C)C)=O)[NH2:10])(OC(C)(C)C)=O.[ClH:19]>C(Cl)Cl.CCO>[ClH:19].[ClH:19].[NH2:10][C:9]([NH2:11])=[NH:8].[NH2:10][C:9]([NH2:11])=[NH:8]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 4124838N,N'-Di-Boc-guanidine

Product 1

HCID 73947521Bis-guanidine dihydrochloride

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

The N′,N″-di-BOCguanidine (0.45 g, 0.60 mmol) was dissolved in CH2Cl2 (10 mL), diluted with dry EtOH (15 mL) and the chilled solution was saturated with dry HCl. The reaction was then kept stirring at room temperature for 3 days (drying tube), when by the product started forming a precipitate over time. After evaporating the solvent to dryness, the residue was washed with ether multiple times and was dried under vacuum at 50-60° C. over night to give whitish yellow solid of the bis-guanidine dihydrochloride; mp>300° C. 1H NMR (DMSO-d6): δ 7.85 (dd, J=1.5, 8.4 Hz, 4H), 7.92 (d, J=1.2 Hz, 4H), 8.00 (dd, J=1.5, 8.4 Hz, 4H), 9.09 (br s, 4H), 11.25 (br s, 2H). 13C NMR (DMSO-d6): δ 155.98, 138.35, 137.32, 135.00, 127.79, 127.22, 124.79. MS (ESI) m/e (rel. int.): 344 (M+, 6), 173 (100). Anal. Calc. for C20H20N6-2.0HCl-1.0H2O-0.2C2H5OH: C %, 55.11; H %, 5.71; N %, 18.90; Found. C %, 55.39; H %, 5.50; N %, 18.71.

Workup

  1. custom(drying tube), when by the product
  2. customstarted forming a precipitate over time
  3. customAfter evaporating the solvent to dryness
  4. washthe residue was washed with ether multiple times
  5. customwas dried under vacuum at 50-60° C. over night

Sources & evidence

ORD record
ord-52792ad2f6104f38a5b694a1e702c074
Source dataset
uspto-grants-2011_06
Patent number
US07964619B2

Reaction notes

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