Thiourea → HCID 58528865, compound

To a solution of (5-acetyl-thiophen-2-yl)-phosphonic acid diethyl ester (1.13 g, 4.31 mmol) in EtOH (80 ml) was added CuBr2 (959 mg, 8.62 mmol). The reaction mixture was then refluxed for 3 hr, diluted with EtOAc, quenched by adding sat. NaHCO3. After layers were separated, the org. layer was collected and the aqueous layer was further extracted with EtOAc once. Combined organic layers were dried over MgSO4, filtrated, and concentrated. The residue was then dissolved in EtOH/EtOAc (4 ml/16 ml) and treated with thiourea (394 mg, 5.17 mmol). The reaction mixture was then heated to reflux for 1 hr, cooled to r.t., and concentrated down. The residue was partitioned between EtOAc and water. The organic layer was collected, dried over MgSO4, filtrated, concentrated, and purified by Biotage to give the final compound (218 mg, 15.9%). 1H NMR (300 MHz, DMSO-d6): δ 7.50 (m, 2H), 7.23 (s, 2H), 7.10 (s, 1H), 4.02 (m, 4H), 1.21 (m, 6H). LC-MS m/z=263.4 [C7H7N2O3PS2+H]+.

1. temperatureThe reaction mixture was then refluxed for 3 hr
2. customquenched
3. additionby adding sat. NaHCO3
4. customAfter layers were separated
5. customlayer was collected
6. extractionthe aqueous layer was further extracted with EtOAc once
7. dry with materialCombined organic layers were dried over MgSO4
8. filtrationfiltrated
9. concentrationconcentrated
10. dissolutionThe residue was then dissolved in EtOH/EtOAc (4 ml/16 ml)
11. temperatureThe reaction mixture was then heated
12. temperatureto reflux for 1 hr
13. concentrationconcentrated down
14. customThe residue was partitioned between EtOAc and water
15. customThe organic layer was collected
16. dry with materialdried over MgSO4
17. filtrationfiltrated
18. concentrationconcentrated
19. custompurified by Biotage

ORD record

ord-507ef4c2ee47416eb6e7e70405c1a26f

Source dataset

uspto-grants-2015_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08940927B2