Chemistry:Cloricromen
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Cloricromen is a platelet aggregation inhibitor.[1] Coronary vasodilator.
Synthesis
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Base catalyzed alkylation of ethyl acetoacetate (1) with 2-chlorotriethylamine (2) gives compound (3). Separately, disulfonation of resorcinol (4) with 96% sulfuric acid gives the disulfonic acid (5). This is chlorinated with potassium chlorate to give 5-chloro-4,6-dihydroxybenzene-1,3-disulfonic acid (6). Removal of the sulfonate groups in dilute acid then gives 2-chlororesorcinol (7).[2] An acid-catalyzed condensation reaction between (3) and (7) produces the intermediate (8). Ether formation at its phenolic hydroxyl group with ethyl bromoacetate (9) completes the synthesis of cloricromen.[3][4]
See also
- Carbocromen is the analogue without the chlorine substituent
References
- ↑ "No effect of cloricromen on some coagulation parameters in patients with ischaemic cerebrovascular disease". The Journal of International Medical Research 22 (5): 287–91. 1994. doi:10.1177/030006059402200506. PMID 7867874.
- ↑ Walton, D. R. M. (1973). "Protection of C-H Bonds". Protective Groups in Organic Chemistry. p. 14. doi:10.1007/978-1-4684-7218-9_1. ISBN 978-1-4684-7220-2.
- ↑ Francesco Della Valle, U.S. Patent 4,452,811 (1984 to Fidia S.P.A.).
- ↑ "Cloricromen". Thieme. https://pharmaceutical-substances.thieme.com/ps/search-results?docUri=KD-03-0223.
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