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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1241960Generated: October 30, 2026

Dimethylformamide → 3-[3-Benzyl-5-(1,3-dimethyl-1,3-dihydrobenzoimidazol-2-ylidene)-4-oxothiazolidin-2-ylideneamino]-4-(ethylamino)benzonitrile

https://huagongshe.com/reaction/1241960

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDimethylformamideHCID 6228—
Reactant1,8-Diazabicyclo(5.4.0)undec-7-eneHCID 81184—
Reactant3-(3-Benzyl-4-oxothiazolidin-2-ylideneamino)-4-ethylaminobenzonitrileHCID 21937376—
Product3-[3-Benzyl-5-(1,3-dimethyl-1,3-dihydrobenzoimidazol-2-ylidene)-4-oxothiazolidin-2-ylideneamino]-4-(ethylamino)benzonitrileHCID 21937564—

Reaction Conditions

Temperature100 °C

Reaction Steps

To a solution of the above salt (66 mg, 0.2 mmol) and 3-(3-benzyl-4-oxothiazolidin-2-ylideneamino)-4-(ethylamino)benzonitrile (70 mg, 0.2 mmol) in DMF was added DBU (62 mL, 2 equiv) and the solution was heated to 100° C. for 48 h. Evaporation of solvent under high vacuum gave a crude, which was purified by chromatography on silica gel eluting with EtOAc-hexane (1:1) to give the title compound (3.6 mg). 1H-NMR indicated one isomer. 1H-NMR (CDCl3): δ 7.46 (2H, m), 7.22–7.36 (8H, m), 6.46 (1H, d), 5.17 (2H, s), 4.44 (1H, t), 3.79 (3H, s), 3.01 (2H, m), 0.88 (3H, t); MS (ESI): 495 (MH+).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07115640B2
Source datasetuspto-grants-2006_10
ORD IDord-cc61170525ff44a4b95a0635f99fe5f6
Source noteuspto-grants-2006_10