One convenient synthesis starts with the O-chloroethyl
ether of p-hydroxybenzamide and proceeds bydisplacement with
imidazole to give 2.
Hydrolysis of the amide function completes the synthesis of dazoxiben.
^DE 2950019, Cross, Peter Edward & Dickinson, Roger Peter, "Imidazolderivate, Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel [Imidazol derivatives, processes for their production and pharmaceuticals containing them]", published 1980-07-10, assigned to
Pfizer Corp.
^Kochergin, P. M.; Palei, R. M.; Balandina, L. V.; Kharitonova, A. E.; Kravchenko, A. N.; Persanova, L. V.; Govorukhina, E. I.; Frolova, M. A. (1995). "Simplified synthesis of dazoxiben". Pharmaceutical Chemistry Journal. 29 (2): 139.
doi:
10.1007/BF02226528.
S2CID37387182.
^Cross, Peter E.; Dickinson, Roger P.; Parry, M. John; Randall, Michael J. (1985). "Selective thromboxane synthetase inhibitors. 1. 1-[(Aryloxy)alkyl]-1H-imidazoles". Journal of Medicinal Chemistry. 28 (10): 1427–1432.
doi:
10.1021/jm00148a009.
PMID3930740.
One convenient synthesis starts with the O-chloroethyl
ether of p-hydroxybenzamide and proceeds bydisplacement with
imidazole to give 2.
Hydrolysis of the amide function completes the synthesis of dazoxiben.
^DE 2950019, Cross, Peter Edward & Dickinson, Roger Peter, "Imidazolderivate, Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel [Imidazol derivatives, processes for their production and pharmaceuticals containing them]", published 1980-07-10, assigned to
Pfizer Corp.
^Kochergin, P. M.; Palei, R. M.; Balandina, L. V.; Kharitonova, A. E.; Kravchenko, A. N.; Persanova, L. V.; Govorukhina, E. I.; Frolova, M. A. (1995). "Simplified synthesis of dazoxiben". Pharmaceutical Chemistry Journal. 29 (2): 139.
doi:
10.1007/BF02226528.
S2CID37387182.
^Cross, Peter E.; Dickinson, Roger P.; Parry, M. John; Randall, Michael J. (1985). "Selective thromboxane synthetase inhibitors. 1. 1-[(Aryloxy)alkyl]-1H-imidazoles". Journal of Medicinal Chemistry. 28 (10): 1427–1432.
doi:
10.1021/jm00148a009.
PMID3930740.