Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dimethylamine | HCID 674 | — |
| Reactant | 1,1'-Carbonyldiimidazole | HCID 68263 | — |
| Reactant | 5-(Tert-butyl)-2-methoxy-3-nitrobenzoic acid | HCID 50882319 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 58493986 | HCID 58493986 | — |
Reaction Steps
44 g 5-tert-butyl-2-methoxy-3-nitro-benzoic acid are dissolved in 400 ml of tetrahydrofuran, combined with 31 g carbonyldiimidazole and stirred for 2 hours at 50° C. The mixture is cooled to ambient temperature, combined with 173 ml of a 2 M solution of dimethylamine in tetrahydrofuran and stirred for a further 16 hours at 50° C. Then it is diluted with ethyl acetate and washed successively with 1 N hydrochloric acid, saturated aqueous sodium hydrogen carbonate solution and saturated aqueous sodium chloride solution. After drying with sodium sulphate the solvents are eliminated in vacuo and the residue is chromatographed on silica gel with chloroform.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08686022B2 |
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| Source dataset | uspto-grants-2014_04 |
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| ORD ID | ord-850b76939ec04e9a91655bc2b9e2d921 |
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| Source note | uspto-grants-2014_04 |
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