Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | 1-(Hexyloxy)-4-isocyanatobenzene | HCID 2769423 | — |
| Reactant | HCID 21920157 | HCID 21920157 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 21920085 | HCID 21920085 | 68.6% |
Reaction Steps
0.67 g (2.14 mmol) of 5-(3′-methylaminobiphenyl-4-ylmethyl)thiazolidine-2,4-dione in 20 ml of dichloromethane is introduced into a 50 ml round-bottomed flask. 1 g (4.3 mmol) of 1-hexyloxy-4-isocyanatobenzene is added and the mixture is heated under reflux for 16 hours. The reaction medium is poured at room temperature over a 1 N HCl solution and extracted with ethyl acetate. The organic phase is washed with water and dried over magnesium sulphate. After evaporation of the solvents, the product obtained is purified by chromatography on silica gel (eluent: heptane/ethyl acetate=3/2). 0.78 g (68%) of 1-[4′-(2,4-dioxothiazolidin-5-ylmethyl)biphenyl-3-yl]-3-(4-hexyloxyphenyl)-1-methylurea is obtained in the form of a white powder having a melting point of 146-148° C.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07294639B2 |
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| Source dataset | uspto-grants-2007_11 |
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| ORD ID | ord-dd068595de564abd8dc08e06b756626e |
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| Source note | uspto-grants-2007_11 |
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