Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Thionyl Chloride | HCID 24386 | — |
| Reactant | 5-Aminophthalide | HCID 720669 | — |
| Reactant | HCID 15410540 | HCID 15410540 | — |
| Solvent | Dimethylacetamide | HCID 31374 | — |
| Product | HCID 15410541 | HCID 15410541 | 38.7% |
Reaction Steps
500 mg of 2-hydroxy-4-phenyl-2-trifluoromethyl-valeric acid (Eur. Appl. 0 253 500 (Imperial Chemical Industries)) in 10 ml of dimethylacetamide is mixed at −15° C. with 0.14 ml of thionyl chloride. After 3 hours of stirring at −15° C., 600 mg of 5-aminophthalide (test) is added. The solution is stirred for 2 hours at −15° C. and then left for 18 hours at room temperature, then mixed with water and extracted with ethyl acetate. The ethyl acetate phase is dried (Na2SO4) and concentrated by evaporation. The residue is stirred with diethyl ether and suctioned off. 290 mg of 5-(2-hydroxy-4-phenyl-2-trifluoromethyl-valeroylamino)-phthalide, melting point 166-168° C., is obtained.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06245804B1 |
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| Source dataset | uspto-grants-2001_06 |
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| ORD ID | ord-2be0728612f541fd8ef57ff3530c2d5c |
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| Source note | uspto-grants-2001_06 |
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