Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | 2-(4-Tert-butylphenoxy)acetic acid | HCID 15718 | — |
| Reactant | 3,5-Diamino-2-methylbenzoic acid | HCID 135524 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Solvent | Trimethyl(phosphooxy)silane | HCID 16133246 | — |
| Product | HCID 178497374 | HCID 178497374 | 221.8% |
Reaction Steps
A mixture of (4-tert-butyl-phenoxy)acetic acid (300 mg, 1.4 mmol), 3,4-diaminobenzoic acid methyl ester (300 mg, 1.4 mmol) in PPSE (4.8 mL) was heated at 160° C. for 4 h. At the end of the reaction period, the mixture was taken to ethyl acetate and neutralized with aqueous sodium bicarbonate. The organic layer was separated and the aqueous solution extracted with ethyl acetate. The combined extracts were dried over anhydrous MgSO4, filtered and the solvent was removed with rotary evaporator under reduced pressure. The residue was purified by flash chromatography (EtOAc:Hexane=1:9˜4:6) to afford 2-2,4-tert-butyl-phenoxymethyl)-1H-benzoimidazole-5-carboxylic acid methyl ester as a colorless powder (547 mg, 80% yield).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08394799B2 |
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| Source dataset | uspto-grants-2013_03 |
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| ORD ID | ord-132a311c25694118be6ef657fa90bf1a |
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| Source note | uspto-grants-2013_03 |
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