Hexamethylenetetramine → 1H-Phenanthro(9,10-d)imidazole

HRID 2058245Notes

Reaction equation

HRID 2058245 reaction equation
[CH:1]1[C:14]2[C:13](=O)[C:12](=O)[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[CH2:17]1[N:22]2CN3CN(C2)C[N:18]1C3.C([O-])(=O)C.[NH4+]>C(O)(=O)C>[N:18]1[C:13]2[C:14]3[C:5]([C:6]4[CH:7]=[CH:8][CH:9]=[CH:10][C:11]=4[C:12]=2[NH:22][CH:17]=1)=[CH:4][CH:3]=[CH:2][CH:1]=3

Participants

5

Reactant 3

HCID 4101HexamethylenetetramineHCID 67639,10-PhenanthrenedioneHCID 517165Ammonium Acetate

Product 1

HCID 674781H-Phenanthro(9,10-d)imidazole

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Phenanthrene-9,10-quinone or an appropriately substituted analog is reacted with hexamethylenetetramine (hexamine) and ammonium acetate in glacial acetic acid to produce the corresponding phenanthro[9,10-d]imidazole. The reaction is carried out with refluxing of the acetic acid. ##STR8## [Edgar A. Stock and A. R. Day, J. Am. Chem. Soc., 65, 452 (1943)].

Sources & evidence

ORD record
ord-21ff1080136048b583ddc0ae8a7d7374
Source dataset
uspto-grants-1980_07
Patent number
US04215135

Reaction notes

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