HuagongsheHuagongshe Chemistry Print Report · For research reference only
N,O-Dimethylhydroxylamine → N-methoxy-N-methylthiazole-4-carboxamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | N,O-Dimethylhydroxylamine | HCID 14232 | — |
| Reactant | 4-Thiazolecarboxylic acid | HCID 304271 | — |
| Reactant | Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) | HCID 9886157 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | N-methoxy-N-methylthiazole-4-carboxamide | HCID 16203794 | — |
Reaction Steps
To a mixture of thiazole-4-carboxylic acid (1 g, 7.74 mmol), N,O-dimethylhydroxylamine (1.51 g, 15.5 mmol), and HATU (3.83 g, 10.07 mmol) in CH2Cl2 (25 mL) was added TEA (4.84 mL, 34.85 mmol). The reaction was stirred at room temperature overnight. The reaction was diluted with CH2Cl2 and water. The organics were concentrated and purified by chromatography (60-70% EtOAc/hexanes) to yield N-methoxy-N-methylthiazole-4-carboxamide as a clear oil. 1H NMR (CDCl3) δ: 8.83 (s, 1H), 8.10 (s, 1H), 3.79 (s, 3H), 3.46 (s, 3H)
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09266835B2 |
| Source dataset | uspto-grants-2016_02 |
| ORD ID | ord-636d70edacf8493cabf42e903c78e1be |
| Source note | uspto-grants-2016_02 |