Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Phenyl chloroformate | HCID 15891 | — |
| Reactant | 5-Ethyl-4-methylthiazol-2-amine | HCID 12735956 | — |
| Reactant | HCID 67274431 | HCID 67274431 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | HCID 42633280 | HCID 42633280 | 33.5% |
Reaction Steps
5-(2-Methoxy-ethyl)-4-methyl-thiophene-2-sulfonic acid amide (0.1556 g, 0.661 mmol) was dissolved in 4 mL of abs. acetonitrile and treated successively with phenyl chloroformate (0.103 g, 1.00 eq.) and triethylamine (0.229 mL, 2.5 eq.), and the mixture kept at ambient temperature for 1 h. The above prepared 5-ethyl-4-methyl-thiazol-2-ylamine (0.094 g, 1.00 eq.), dissolved in a tiny amount of acetonitrile, was then added, and the mixture heated to 60° C. over night. Cooling, pouring onto crashed ice/NH4Cl, twofold extraction with ethyl acetate, washing with brine, drying over magnesium sulfate, and evaporation of the solvents, followed by flash chromatography (SiO2, ethyl acetate), yielded eventually 0.089 g of the title compound as light brown solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07973051B2 |
|---|
| Source dataset | uspto-grants-2011_07 |
|---|
| ORD ID | ord-e5944f0881a4462b8ecb4ae049f4815d |
|---|
| Source note | uspto-grants-2011_07 |
|---|