Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Pyridine | HCID 1049 | — |
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | Phenyl chloroformate | HCID 15891 | — |
| Reactant | 4-Amino-2-chlorobenzonitrile | HCID 88728 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 60630334 | HCID 60630334 | 91.7% |
Reaction Steps
Dissolve 4-amino-2-chloro-benzonitrile (500 mg, 3.3 mmol) and pyridine (518 mg, 6.6 mmol) in THF (5 mL), cool to 0° C. and add slowly phenyl chloroformate (616 mg, 3.9 mmol). After addition, stir the reaction at room temperature for 2 hrs. TLC (EtOAc:PE=1:3) shows the reaction is complete. Add water, extract with DCM, separate the organic layer. Wash the organic layer with 1M HCl solution, brine sequentially, dry over anhydrous Na2SO4, and concentrate under reduced pressure to give the target compound (820 mg, 91.7%). MS: (M+1): 273.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09359338B2 |
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| Source dataset | uspto-grants-2016_06 |
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| ORD ID | ord-cb38a28c641247d189b9dd20afc1e933 |
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| Source note | uspto-grants-2016_06 |
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