HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sulfuryl chloride → 5-Chloro-3-(2,5-dichloro-pyrimidin-4-ylamino)-4-methyl-thiophene-2-carboxylic acid methylamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sulfuryl chloride | HCID 24648 | — |
| Reactant | 3-(2,5-dichloropyrimidin-4-ylamino)-N,4-dimethylthiophene-2-carboxamide | HCID 86634019 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 5-Chloro-3-(2,5-dichloro-pyrimidin-4-ylamino)-4-methyl-thiophene-2-carboxylic acid methylamide | HCID 86634079 | 9% |
Reaction Steps
An ice-cold solution of 3-(2,5-dichloro-pyrimidin-4-ylamino)-4-methyl-thiophene-2-carboxylic acid methylamide (0.105 g, 0.33 mmol) in methylene chloride (4 mL) was treated with sulfuryl chloride (33 μL). The mixture was stirred for 16 hours and concentrated. Chromatography on preparative TLC plate (hexanes/ethyl acetate/methanol (50:25:1)) gave 5-chloro-3-(2,5-dichloro-pyrimidin-4-ylamino)-4-methyl-thiophene-2-carboxylic acid methylamide (10.4 mg, 9%): 1H NMR (300 MHz, CDCl3) δ 9.9 (s, 1H), 8.33 (s, 1H), 5.82 (br, 1H), 3.05 (d, 3H), 2.22 (s, 3H); MS (m/e): 351.1 (M+1).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08148391B2 |
| Source dataset | uspto-grants-2012_04 |
| ORD ID | ord-bbcf03e2a15b4b2fbcb2edffeeaf8b25 |
| Source note | uspto-grants-2012_04 |