HuagongsheHuagongshe Chemistry Print Report · For research reference only
Thionyl Chloride → HCID 70221743, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Thionyl Chloride | HCID 24386 | — |
| Reactant | 5-Chloro-2-oxo-2,3-dihydro-1H-indole-1-carboxamide | HCID 9859159 | — |
| Reactant | HCID 15007375 | HCID 15007375 | — |
| Reactant | 5-(Chlorocarbonyl)thiophen-3-yl acetate | HCID 21266020 | — |
| Catalyst | 4-(Dimethylamino)pyridine | HCID 14284 | — |
| Solvent | Acetic Acid | HCID 176 | — |
| Product | HCID 70221743 | HCID 70221743 | 82% |
Reaction Steps
The title compound was prepared according to the procedure of Example 32. The reaction of 15 ml of thionyl chloride with 3.58 g (19.23 mmoles) of 4-acetoxy-2-thiophenecarboxylic acid (prepared according to Bohlmann, F., et al., Chem. Ber. 106:497 (1973)) gave a yellow oil. A 3.32 g (16.22 mmoles) sample of 4-acetoxy-2-thiophenecarbonyl chloride was coupled to 2.85 g (13.52 mmoles) of 5-chloro-2-oxindole-1-carboxamide in the presence of 4.16 g (34.07 mmoles) 4-(N,N-dimethylamino)pyridine to give 5.40 g of crude yellow product. Purification by recrystallization gave 4.18 g (11.02 mmoles, 82%) of pure title compound as a yellow solid, m.p. 222°-224° C. (acetic acid).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05290802 |
| Source dataset | uspto-grants-1994_03 |
| ORD ID | ord-74599eac214b45dcacd788c605c759d0 |
| Source note | uspto-grants-1994_03 |