HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium Carbonate → 4-Chloro-7,8-dimethyl-imidazo[1,2-a]quinoxaline
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | Ethane, 2-bromo-1,1-diethoxy- | HCID 74852 | — |
| Reactant | Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) | HCID 466102 | — |
| Reactant | 3-Chloro-6,7-dimethyl-quinoxalin-2-ylamine | HCID 85659213 | — |
| Solvent | Oxolane--water (1/1) | HCID 21881883 | — |
| Product | 4-Chloro-7,8-dimethyl-imidazo[1,2-a]quinoxaline | HCID 86665324 | 67.4% |
Reaction Steps
To a stirred suspension of 3-chloro-6,7-dimethyl-quinoxalin-2-ylamine (30.9 g, 0.16 mol) in water/THF 1:1 (540 mL) at room temperature was added bromoacetaldehyde diethyl acetal (94.6 g, 0.48 mol) and 5 g of PPTS in one portion. After stirring at room temperature for 1 h, the mixture was heated to reflux for 3 h under stirring and then stirred for an additional 15 h at room temperature. The pH value of the mixture was adjusted to pH 8 by addition of solid sodium carbonate. The precipitate formed was filtered off to give 25 g of the title compound. 1H-NMR (300 MHz, d6-DMSO): δ=8.85 (1H, s), 8.19 (1H, s), 7.73 (1H, bs), 7.80 (1H, bs), 3.60 (6H, s) ppm.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08729082B2 |
| Source dataset | uspto-grants-2014_05 |
| ORD ID | ord-27ad3a4c5ccd4239b9cd8f6df08ecdf8 |
| Source note | uspto-grants-2014_05 |