HuagongsheHuagongshe Chemistry Print Report · For research reference only
Carbon Dioxide → 7-Benzyloxy-2-methyl-3-(2-trimethylsilanyl-ethoxymethyl)-3H-benzimidazole-5-carboxylic Acid Dimethylamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Carbon Dioxide | HCID 280 | — |
| Reactant | Dimethylamine | HCID 674 | — |
| Reactant | Triphenylphosphine | HCID 11776 | — |
| Reactant | 4-Benzyloxy-6-bromo-2-methyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-benzimidazole | HCID 46221162 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Product | 7-Benzyloxy-2-methyl-3-(2-trimethylsilanyl-ethoxymethyl)-3H-benzimidazole-5-carboxylic Acid Dimethylamide | HCID 46221163 | 65% |
Reaction Steps
5.8 g (13 mmol) 4-Benzyloxy-6-bromo-2-methyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-benzimidazole, 1.3 g (5.2 mmol) triphenylphosphine, 0.4 g (1.9 mmol) palladium(II) acetate and 80 ml (160 mmol) dimethylamine (2M in THF) were transferred to an autoclave and carbonylated (6 bar CO2) at 120° C. for 16 h. The catalyst was filtered off and the filtrate was concentrated in vacuo. The crystallization of the residue from diisopropyl ether afforded 3.7 g (65%) of the title compound as a white solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07307084B2 |
| Source dataset | uspto-grants-2007_12 |
| ORD ID | ord-4012a087390c4199acd52f25c093bb2d |
| Source note | uspto-grants-2007_12 |