Tris(3-aminopropyl)amine → Tris(3-[([(3,5-diacetylphenyl)amino]carbonyl)amino]propyl)amine

HRID 613833Notes

Reaction equation

HRID 613833 reaction equation
Cl.Cl.Cl.Cl.Cl.Cl.Cl.C(NN=C(NCCCN(CCCN[C:75]([NH:77][C:78]1[CH:83]=[C:82]([C:84](=[O:86])[CH3:85])[CH:81]=[C:80]([C:87](=[O:89])[CH3:88])[CH:79]=1)=[O:76])CCCNC(=NNC(=N)N)NC1C=C(C(=NNC(=N)N)C)C=C(C(=NNC(=N)N)C)C=1)NC1C=C(C(=NNC(=N)N)C)C=C(C(=NNC(=N)N)C)C=1)(=N)N.[C:90]([C:93]1[CH:94]=[C:95]([N:102]=[C:103]=[O:104])[CH:96]=[C:97]([C:99](=[O:101])[CH3:100])[CH:98]=1)(=[O:92])[CH3:91].[NH2:105][CH2:106][CH2:107][CH2:108][N:109]([CH2:114][CH2:115][CH2:116][NH2:117])[CH2:110][CH2:111][CH2:112][NH2:113]>O1CCCC1>[C:99]([C:97]1[CH:96]=[C:95]([NH:102][C:103]([NH:105][CH2:106][CH2:107][CH2:108][N:109]([CH2:114][CH2:115][CH2:116][NH:117][C:75]([NH:77][C:78]2[CH:79]=[C:80]([C:87](=[O:89])[CH3:88])[CH:81]=[C:82]([C:84](=[O:86])[CH3:85])[CH:83]=2)=[O:76])[CH2:110][CH2:111][CH2:112][NH:113][C:75]([NH:77][C:78]2[CH:83]=[C:82]([C:84](=[O:86])[CH3:85])[CH:81]=[C:80]([C:87](=[O:89])[CH3:88])[CH:79]=2)=[O:76])=[O:104])[CH:94]=[C:93]([C:90](=[O:92])[CH3:91])[CH:98]=1)(=[O:101])[CH3:100]

Participants

5

Reactant 3

HCID 547030Tris(3-aminopropyl)amineHCID 155412853,5-Diacetylphenyl isocyanateHCID 178466969Tris(3-[([(3,5-diacetylphenyl)amino]carbonyl)amino]propyl)amine hexakis(amidinohydrazone) heptahydrochloride

Product 1

HCID 21195014Tris(3-[([(3,5-diacetylphenyl)amino]carbonyl)amino]propyl)amine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Compound 36, FIG. 7H.36: 3,5-Diacetylphenyl isocyanate (0.4 g) and tris(3-aminopropyl)amine (0.12 g) in tetrahydrofuran (5 mL) were stirred at r.t. for 30 min. Filtration gave 0.32 g of tris(3-[([(3,5-diacetylphenyl)amino]carbonyl)amino]propyl)amine, mp 147-8 C. This hexaketone (0.4 g) and aminoguanidine dihydrochloride (0.49 g) were heated in methanol (3 mL) for 4 hours. Addition of ethanol and filtration gave 0.58 g of tris(3-[([(3,5-diacetylphenyl)amino]carbonyl)amino]propyl)amine hexakis(amidinohydrazone) heptahydrochloride (Compound 36) as the dihydrate hemi-ethanolate, mp 250-1° C. (dec).

Workup

  1. filtrationFiltration

Sources & evidence

ORD record
ord-32af1b9080fc491d83f05974c0fd16a3
Source dataset
uspto-grants-1999_12
Patent number
US06008255

Reaction notes

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