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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1062673Generated: October 26, 2026

Diethyl Ether → 2-Amino-4-(3-cyanophenyl)-5-carboethoxythiazole

https://huagongshe.com/reaction/1062673

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDiethyl EtherHCID 3283—
ReactantThioureaHCID 2723790—
ReactantEthyl 2-bromo-3-(3-cyanophenyl)-3-oxopropionateHCID 22282470—
SolventTetrahydrofuranHCID 8028—
Product2-Amino-4-(3-cyanophenyl)-5-carboethoxythiazoleHCID 22282485102.7%

Reaction Conditions

Temperature65 °C

Reaction Steps

To a solution of ethyl 2-bromo-3-(3-cyanophenyl)-3-oxopropionate (4.0 g, 13.5 mmol) in 100 mL of tetrahydrofuran was added thiourea (1.03 g, 13.5 mmol). The resulting mixture was stirred at 65° C. for 16 h. The reaction was allowed to cool and the solvent was evaporated in vacuo. The residue was triturated with ether, taken up in ethyl acetate, washed with saturated aq Na2CO3 and brine, dried (MgSO4) and concentrated in vacuo to yield a solid. Trituration with ethyl ether left the title compound as an off-white solid (3.79 g, 98%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS06962935B2
Source datasetuspto-grants-2005_11
ORD IDord-d19b10cfcc5e4f20aba60ec8af47cc49
Source noteuspto-grants-2005_11