Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Phosphorus oxychloride | HCID 24813 | — |
| Reactant | 5-Methyl-3-phenyl-4-isoxazolecarbohydrazide | HCID 727924 | — |
| Reactant | HCID 67215476 | HCID 67215476 | — |
| Solvent | Chlorobenzene | HCID 7964 | — |
| Product | HCID 67215347 | HCID 67215347 | 78% |
Reaction Steps
To a suspension of 5-methyl-3-phenyl-isoxazole-4-carboxylic acid hydrazide (200 mg, 0.92 mmol) in chlorobenzene (2 mL) was added 5-(imidazole-1-carbonyl)-1,3-dihydro-benzoimidazol-2-one (315 mg, 1.38 mmol) and stirred for 18 h at 100° C. After cooling to ambient temperature phosphorus oxychloride (126 μL, 1.38 mmol) was added and the suspension was stirred for 4 h at 100° C. It was then cooled to ambient temperature and water (2 mL) was added, stirred for 15 min, and the resulting precipitate filtered off and washed with water (5 mL) and tert-butylmethylether (5 mL). Recrystallisation from ethanol afforded the title compound (257 mg, 78%) which was obtained as a light-grey solid. MS: m/e=360.1 [M+H]+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07541372B2 |
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| Source dataset | uspto-grants-2009_06 |
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| ORD ID | ord-8911bb53a02f4e6fa41ff1e84cb0f4db |
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| Source note | uspto-grants-2009_06 |
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