HuagongsheHuagongshe Chemistry Print Report · For research reference only
Pyridine → {4-[4-(5-Bromo-pyridin-2-ylcarbamoyl)-2-nitro-phenylsulfanyl]-phenyl}-carbamic acid 2,2,2-trichloro-ethyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Pyridine | HCID 1049 | — |
| Reactant | 2,2,2-Trichloroethyl chloroformate | HCID 87063 | — |
| Reactant | 4-(4-Amino-phenylsulfanyl)-N-(5-bromo-pyridin-2-yl)-3-nitro-benzamide | HCID 67040091 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | {4-[4-(5-Bromo-pyridin-2-ylcarbamoyl)-2-nitro-phenylsulfanyl]-phenyl}-carbamic acid 2,2,2-trichloro-ethyl ester | HCID 67040335 | 92% |
Reaction Steps
A mixture of the product of Example 364B (27.5 g, 0.0618 mol) and pyridine (7.73 g, 7.50 mL, 0.0927 mol, 1.5 equiv.) in dichloromethane (500 mL) was stirred at room temperature. To this mixture was added slowly, dropwise 2,2,2-trichloroethyl chloroformate (17.0 g, 10.8 mL, 0.0803 mol, 1.3 equiv.) over 30 minutes. The reaction mixture was stirred at room temperature for 2 hours, during which time the product precipitated as a yellow solid. The mixture was filtered and the filter cake was rinsed with dichloromethane (100 mL) and dried in vacuo to give the title compound (35.3 g, 92%) as a yellow solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07910595B2 |
| Source dataset | uspto-grants-2011_03 |
| ORD ID | ord-8447e5aacf4645fa948a0a178fd92265 |
| Source note | uspto-grants-2011_03 |