Cloricromen

Cloricromen

Clinical data
ATC code	B01AC02 (WHO)
Identifiers
IUPAC name Ethyl 2-(8-chloro-3-(2-(diethylamino)ethyl)-4-methyl-2-oxo-2H-chromen-7-yloxy)acetate
CAS Number	68206-94-0
PubChem CID	68876
ChemSpider	62108^Y
UNII	B9454PE93C
KEGG	D07139^Y
ChEMBL	ChEMBL255066^Y
CompTox Dashboard (EPA)	DTXSID2048373
ECHA InfoCard	100.164.003
Chemical and physical data
Formula	C20H26ClNO5
Molar mass	395.88 g·mol^−1
3D model (JSmol)	Interactive image
SMILES O=C(OCC)COc2ccc\1c(OC(=O)/C(=C/1C)CCN(CC)CC)c2Cl
InChI InChI=1S/C20H26ClNO5/c1-5-22(6-2)11-10-15-13(4)14-8-9-16(26-12-17(23)25-7-3)18(21)19(14)27-20(15)24/h8-9H,5-7,10-12H2,1-4H3^Y Key:GYNNRVJJLAVVTQ-UHFFFAOYSA-N^Y

Cloricromen is a platelet aggregation inhibitor.^[1] Coronary vasodilator.

Synthesis

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

1. Orefice G, Grasso A, Fazio N, Del Vecchio G, Volpe G, Coppola M, D'Alessio A, Carrieri PB (1994). "No effect of cloricromen on some coagulation parameters in patients with ischaemic cerebrovascular disease". The Journal of International Medical Research. 22 (5): 287–91. doi:10.1177/030006059402200506. PMID 7867874. S2CID 36081514.
2. 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.
3. Francesco Della Valle, U.S. patent 4,452,811 (1984 to Fidia S.P.A.).
4. "Cloricromen". Thieme.