Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | 2-(5-Dimethoxymethyl-2-nitro-phenylamino)-4-(2-trifluoromethyl-phenyl)-thiazole-5-carboxylic acid amide | HCID 86642817 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | HCID 86642818 | HCID 86642818 | 66.8% |
Reaction Steps
A solution of 0.23 g (0.48 mmole) of 2-(5-dimethoxymethyl-2-nitro-phenylamino)-4-(2-trifluoromethyl-phenyl)-thiazole-5-carboxylic acid amide (VI.17a) in 9 mL mixture of acetonitrile and 2M hydrochloric acid (2:1) was heated at 60 degrees for 3 hours, cooled and concentrated under reduced pressure. The residue was diluted with dichloromethane and saturated sodium bicarbonate. The solid was collected by filtration, washed with water and dried to give 0.14 g of 2-(5-formyl-2-nitro-phenylamino)-4-(2-trifluoromethyl-phenyl)-thiazole-5-carboxylic acid amide (VI.17b) as an orange solid. The filtrate was extracted twice with dichloromethane. The combined dichloromethane layers were washed with brine, dried over anhydrous sodium sulfate, concentrated under reduced pressure to give additional product of 0.046 g as an orange solid. The combined material was used directly in the next step without further purification.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08044213B2 |
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| Source dataset | uspto-grants-2011_10 |
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| ORD ID | ord-d3d9e4806cc94012aacbfa48e7041d24 |
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| Source note | uspto-grants-2011_10 |
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