Potassium Carbonate → 1-Dimethylaminomethylene-3-(3-methanesulfonyl-phenyl)-thiourea

To a solution of 7.47 g (36 mmol) 3-Methylsulfonyl aniline hydrochloride and 6.15 ml diisopropylethylamine in 75 ml THF was added 5.87 g (36 mmol) benzoyl isothiocyanate dropwise and allowed to stir at room temperature for 1 h. The volatiles were removed under reduced pressure and the residue was treated with diethyl ether. The precipitate was filtered off, dried and dissolved in 100 ml THF and 130 ml methanol. 18 g (130 mmol) potassium carbonate in 45 ml water was added and the mixture was stirred for 24 h at room temperature. The reaction mixture was concentrated and diluted with water. The precipitate was filtered off, washed with diethyl ether/ethanol and dried. The crude solid was dissolved in 50 ml dimethylformamide dimethyl acteal and heated for 3 h to 90° C. The precipitate was filtered off, washed with THF and dried to obtain 9.3 g (90%) of the title compound as white solid.

1. customThe volatiles were removed under reduced pressure
2. additionthe residue was treated with diethyl ether
3. filtrationThe precipitate was filtered off
4. customdried
5. dissolutiondissolved in 100 ml THF
6. stirringthe mixture was stirred for 24 h at room temperature
7. concentrationThe reaction mixture was concentrated
8. additiondiluted with water
9. filtrationThe precipitate was filtered off
10. washwashed with diethyl ether/ethanol
11. customdried
12. dissolutionThe crude solid was dissolved in 50 ml dimethylformamide dimethyl acteal
13. temperatureheated for 3 h to 90° C
14. filtrationThe precipitate was filtered off
15. washwashed with THF
16. customdried

ORD record

ord-32ff2a43bb714494969a2c64d150c9fd

Source dataset

uspto-grants-2007_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07253197B2