HuagongsheHuagongshe Chemistry Print Report · For research reference only
Dimethylformamide → 3-{3,5-Dimethyl-4-[6-(5-o-tolyl-[1,3,4]oxadiazol-2-yl)-1H-benzoimidazol-2-yl]-phenyl}-2,2-dimethyl-propionic acid
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | 3,4-Diaminobenzoic acid | HCID 69263 | — |
| Reactant | Potassium hydroxy sulfite | HCID 23707502 | — |
| Reactant | 2-[4-(2-Methoxycarbonyl-2-methyl-propyl)-2,6-dimethyl-phenyl]-3H-benzoimidazole-5-carboxylic acid | HCID 66966766 | — |
| Reactant | Methyl 3-(4-formyl-3,5-dimethylphenyl)-2,2-dimethylpropanoate | HCID 86632822 | — |
| Solvent | Water | HCID 962 | — |
| Product | 3-{3,5-Dimethyl-4-[6-(5-o-tolyl-[1,3,4]oxadiazol-2-yl)-1H-benzoimidazol-2-yl]-phenyl}-2,2-dimethyl-propionic acid | HCID 25235459 | — |
Reaction Steps
2-[4-(2-Methoxycarbonyl-2-methyl-propyl)-2,6-dimethyl -phenyl]-3H-benzoimidazole-5-carboxylic acid. 7.6 g of 3,4-diaminobenzenoic acid was stirred in 120 ml of DMF at room temperature. It was treated with 12.4 g of 3-(4-formyl-3,5-dimethyl-phenyl)-2,2-dimethyl-propionic acid methyl ester (the intermediate A in Example 1-62) followed by an addition of a slurry of 15 g of Oxone in 60 ml of DMF. The reaction was stirred at room temperature for 3 h and 60 mL of water was added and the pH was adjusted to 6. Additional 150 mL of water was added and the resulting precipitates were collected by filtration. The collected precipitates were washed with water and dried under vacuum to afford the title compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08217065B2 |
| Source dataset | uspto-grants-2012_07 |
| ORD ID | ord-42dacf1cf08b47f9b477799528c38d48 |
| Source note | uspto-grants-2012_07 |