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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1468678Generated: November 2, 2026

Ethyl Acetate → 7-(4-Chlorophenyl)-5-methyl-6-vinylbenzo[d]thiazole

https://huagongshe.com/reaction/1468678

Reaction equation

Participants

RoleNameHCIDCharge
ReactantEthyl AcetateHCID 8857—
ReactantLithium ChlorideHCID 433294—
ReactantTri(butyl)vinyltinHCID 53438229—
Reactant7-(4-Chlorophenyl)-5-methylbenzo[d]thiazol-6-yl trifluoromethanesulfonateHCID 89157565—
CatalystHCID 178418476HCID 178418476—
SolventDimethylformamideHCID 6228—
Product7-(4-Chlorophenyl)-5-methyl-6-vinylbenzo[d]thiazoleHCID 89157799—

Reaction Conditions

Temperature120 °C

Reaction Steps

7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-6-yl trifluoromethanesulfonate (5F) from above reaction was dissolved in DMF (3 ml). Tributylvinyltin (130 uL), PdCl2(PPh3)2 (27 mg, 0.039 mmol) and LiCl (49 mg, 1.17 mmol) were added. The reaction mixture was stirred at 120° C. in microwave for 30 min. The reaction mixture was diluted by ethyl acetate, washed with saturated NaHCO3 solution and extracted with ethyl acetate. The organic layer was dried over MgSO4, filtered, concentrated and purified by silica gel column (0-50% ethyl acetate/hexanes). LCMS-ESI+: calc'd for C16H20ClNS: 286.0 (M+H+). Found: 286.1 (M+H+).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09006229B2
Source datasetuspto-grants-2015_04
ORD IDord-938b1ac069b44827a5d61c45e54dba23
Source noteuspto-grants-2015_04