HuagongsheHuagongshe Chemistry Print Report · For research reference only
Pyridine → Methyl 3-[2,6-dichloro-4-(trifluoromethyl)phenylsulfonamido]thiophene-2-carboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Pyridine | HCID 1049 | — |
| Reactant | Methyl 3-amino-2-thiophenecarboxylate | HCID 89652 | — |
| Reactant | 2,6-Dichloro-4-(trifluoromethyl)benzenesulfonyl chloride | HCID 2736869 | — |
| Catalyst | 4-(Dimethylamino)pyridine | HCID 14284 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | Methyl 3-[2,6-dichloro-4-(trifluoromethyl)phenylsulfonamido]thiophene-2-carboxylate | HCID 67520512 | 69.9% |
Reaction Steps
Synthesized as described for 3 using 2,6-dichloro-4-(trifluoromethyl)benzene-1-sulfonyl chloride (2.5 g; 7.97 mmol), methyl 3-aminothiophene-2-carboxylate (1.14 g; 7.25 mmol), 4-dimethylaminopyridine (221.4 mg; 1.81 mmol), pyridine (11.81 mL; 145.0 mmol) and anhydrous dichloromethane (50 mL). Purification by automated silica gel chromatography (Biotage®) eluting with ethyl acetate/hexanes (0 to 30% v/v over 400 mL gradient elution) afforded the title compound as a white solid (2.20 g).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08178699B2 |
| Source dataset | uspto-grants-2012_05 |
| ORD ID | ord-6a68a64b3b484acb9b941d922a57dabf |
| Source note | uspto-grants-2012_05 |