HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium Carbonate → 1-{3-[(1,3-Benzothiazol-2-yl)methoxy]phenyl}pyrrolidine-2,5-dione
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 2-(Chloromethyl)benzothiazole | HCID 304978 | — |
| Reactant | Methyl 4-(3-hydroxyanilino)-4-oxobutanoate | HCID 13491817 | — |
| Catalyst | Potassium Iodide | HCID 4875 | — |
| Solvent | Acetone | HCID 180 | — |
| Product | 1-{3-[(1,3-Benzothiazol-2-yl)methoxy]phenyl}pyrrolidine-2,5-dione | HCID 13491818 | 60.9% |
Reaction Steps
A mixture of 4-[[3-(hydroxy)phenyl]amino]-4-oxobutanoic acid, methyl ester (1.45 g, 6.5 mmol), 2-chloromethylbenzothiazole (1.20 g, 6.5 mmol), cesium carbonate (1.0 g), sodium carbonate (0.7 g), potassium iodide (5 mg) and acetone (60 ml) is heated at reflux for 2 hours. The reaction is filtered through a pad of Celite and silica gel and the solvent is removed in vacuo. Recrystallization from acetone gives 1.34 g (56% yield) of product, m.p. 175°-176° C.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US04550172 |
| Source dataset | uspto-grants-1985_10 |
| ORD ID | ord-344a4a7e534e487d9fdbceb644f876a5 |
| Source note | uspto-grants-1985_10 |