HuagongsheHuagongshe Chemistry Print Report · For research reference only
Dimethylformamide dimethyl acetal → Methyl 5-(4-chlorophenyl)-3-(dimethylaminomethyleneamino)thiophene-2-carboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Dimethylformamide dimethyl acetal | HCID 78373 | — |
| Reactant | Methyl 3-amino-5-(4-chlorophenyl)thiophene-2-carboxylate | HCID 2777492 | — |
| Solvent | Ethanol | HCID 702 | — |
| Product | Methyl 5-(4-chlorophenyl)-3-(dimethylaminomethyleneamino)thiophene-2-carboxylate | HCID 11544322 | — |
Reaction Steps
The title compound was prepared following the procedure described in WO2003/033476. Condensation of 2.00 g of methyl 3-amino-5-(4-chlorophenyl)thiophene-2-carboxylate with dimethylformamide dimethyl acetal for 3 hr in refluxing EtOH yielded 2.52 g (100%) after removal of the volatiles under vacuum. 1H NMR (CDCl3) δ 3.06 (s, 3H), 3.08 (s, 3H), 3.81 (s, 3H), 6.98 (s, 1H), 7.35 (d, J=8.79 Hz, 2H), 7.53 (d, J=8.24 Hz, 2H), 7.69 (s, 1H); 13C NMR (CDCl3) δ 34.31, 40.26, 51.44, 112.43, 122.28, 126.95, 129.09, 132.18, 134.45, 145.79, 156.09, 159.16, 163.22. HPLC (Method #1): 2.45 min retention time. MS (ES): m/z 323 [M+H]+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07745447B2 |
| Source dataset | uspto-grants-2010_06 |
| ORD ID | ord-cb41392dda644435b7f55830f1023776 |
| Source note | uspto-grants-2010_06 |