HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → HCID 178497007, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Cyanogen Bromide | HCID 10476 | — |
| Reactant | Methyl 4,5-diamino-2,2-dimethyl-2,3-dihydro-1-benzofuran-7-carboxylate | HCID 67503724 | — |
| Solvent | Ethanol | HCID 702 | — |
| Product | HCID 178497007 | HCID 178497007 | 45.2% |
Reaction Steps
To a solution of methyl 4,5-diamino-2,2-dimethyl-2,3-dihydro-1-benzofuran-7-carboxylate (Intermediate-1, 2.00 g, 8.47 mmol) in ethanol:water (50:4 mL) was added cyanogen bromide (1.07 g, 10.16 mmol). The reaction mass was refluxed for 4-5 h. The reaction mass was quenched in water, neutralised with sodium bicarbonate and extracted with solution of (10%) DCM: methanol. The organic layer was dried over anhydrous sodium sulphate and concentrated to afford 1.0 g of the desired product. 1HNMR (DMSO-d6): δ 1.42 (s, 6H), 3.03 (s, 2H), 3.71 (s, 3H), 6.67 (bs, 2H), 7.33 (s, 1H), 10-11 (bs, 1H). MS [M+H]+: 237.03.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08519149B2 |
| Source dataset | uspto-grants-2013_08 |
| ORD ID | ord-ded34e6e3ec645db9daa96b5f2afe03b |
| Source note | uspto-grants-2013_08 |