Hydrochloric Acid → HCID 178478783, compound

HRID 1170463Notes

Reaction equation

HRID 1170463 reaction equation
C([N:8]=[C:9]([NH:42]C(OC(C)(C)C)=O)[NH:10][C:11]1[CH:23]=[CH:22][C:21]2[C:20]3[C:15](=[CH:16][C:17]([NH:24][C:25]([NH:34]C(OC(C)(C)C)=O)=[N:26]C(OC(C)(C)C)=O)=[CH:18][CH:19]=3)[CH2:14][C:13]=2[CH:12]=1)(OC(C)(C)C)=O.[ClH:50]>C(Cl)Cl.CCO>[ClH:50].[ClH:50].[NH:10]([C:11]1[CH:23]=[CH:22][C:21]2[C:20]3[C:15](=[CH:16][C:17]([NH:24][C:25]([NH2:34])=[NH:26])=[CH:18][CH:19]=3)[CH2:14][C:13]=2[CH:12]=1)[C:9]([NH2:42])=[NH:8]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 178454278HCID 178454278, compound

Product 1

HCID 178478783HCID 178478783, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

The N′,N″-di-BOC-guanidine (4a) (0.25 g, 0.4 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 (0.13 g, quantitative), mp>340° C. 1H-NMR (DMSO-d6): δ 3.95 (s, 2H), 7.24 (d, J=8.4 Hz, 2H), 7.45 (s, 2H), 7.58 (br s, 8H), 7.95 (d, J=8.4 Hz, 2H), 10.23 (br s, 2H). 13C-NMR (DMSO-d6): δ 156.1, 156.1, 144.5, 138.6, 133.8, 123.3, 121.4, 120.9, 36.8. MS (EI): m/z 277 (M++1) (14), 252 (100). Anal. Calcd. for C15H16N6.2HCl-0.25C2H5OH (364.76): C % 51.04, H % 5.39, N % 23.04, Cl % 19.44. Found: C % 50.74, H % 5.26, N % 22.99, Cl % 19.87.

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-0fc11e2c7c114d0988cbd30fe353ab94
Source dataset
uspto-grants-2010_11
Patent number
US07825279B2

Reaction notes

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