Cloricromen

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

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

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