HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1619271Generated: October 31, 2026
Thionyl Chloride → 2-Chloro-5-benzoxazolecarbonitrile
https://huagongshe.com/reaction/1619271
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Thionyl Chloride | HCID 24386 | — |
| Reactant | 2-Thioxo-2,3-dihydro-1,3-benzoxazole-5-carbonitrile | HCID 10511479 | — |
| Catalyst | Dimethylformamide | HCID 6228 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 2-Chloro-5-benzoxazolecarbonitrile | HCID 10631180 | 65% |
Reaction Steps
To a mixture of 2-thioxo-2,3-dihydrobenzooxazole-5-carbonitrile (2.56 g, 14.5 mmol) and thionylchloride (14.1 mL) was added two drops of DMF. The mixture was heated at 65-70° C. for 1 h. Then the mixture was cooled to rt and diluted with CH2Cl2. The solvent and excess thionylchloride were removed under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: 20% EtOAc in Petroleum ether) to give 2-chlorobenzo-oxazole-5-carbonitrile 1.69 g (65%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08772285B2 |
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| Source dataset | uspto-grants-2014_07 |
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| ORD ID | ord-2bf63788ebd64e0abb69a8badfc68823 |
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| Source note | uspto-grants-2014_07 |
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