Hydrochloric Acid → 1-[5-(Amidino)-tetralin-1-ylideneamino]-2-amino-4,5-dihydro-imidazole dihydrochloride

HRID 357623Notes

Reaction equation

HRID 357623 reaction equation
[ClH:1].Cl.[C:3]([C:6]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:7]=1[CH2:8][CH2:9][CH2:10][C:11]2=O)(=[NH:5])[NH2:4].Cl.[NH2:18][N:19]1[CH2:23][CH2:22][N:21]=[C:20]1[NH2:24]>C(O)(C)C>[ClH:1].[ClH:1].[C:3]([C:6]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:7]=1[CH2:8][CH2:9][CH2:10][C:11]2=[N:18][N:19]1[CH2:23][CH2:22][N:21]=[C:20]1[NH2:24])(=[NH:5])[NH2:4]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 189379125-Amidino-1-tetralone hydrochlorideHCID 189379401,2-Diamino-4,5-dihydro-imidazole hydrochloride

Product 1

HCID 699055171-[5-(Amidino)-tetralin-1-ylideneamino]-2-amino-4,5-dihydro-imidazole dihydrochloride

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

0.2 ml of 32% hydrochloric acid (Merck, Darmstadt, Germany; p.a.) is added, with stirring, to a solution of 0.25 g (0.001 mol) of 5-(amidino)-1-tetralone hydrochloride and 0.136 g (0.001 mol) of 1,2-diamino-4,5-dihydro-imidazole hydrochloride in 5 ml of iso-propanol, and the mixture is stirred at 80°-90° C. for 16 hours. The reaction mixture is filtered while hot and the filtration product is washed with isopropanol and dried, yielding the title compound, m.p. >220° C. (decomp.), 1H-NMR (DMSO/D2O): δ=8.15 (d, 1H); 7.67 (d, 1H); 7.55 (t, 1H); 4.17 (t, 2H); 3.68 (t, 2H); 3.23 (m, 2H); 3.15 (m, 2H); 1.9 (m, 2H).

Workup

  1. filtrationThe reaction mixture is filtered while hot and the filtration product
  2. washis washed with isopropanol
  3. customdried

Sources & evidence

ORD record
ord-695241ce97ac4e558e020545e1134896
Source dataset
uspto-grants-1998_11
Patent number
US05840911

Reaction notes

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