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With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 0 - 25℃; for 2.5 h; Industrial scale
32.2 g of 5-methanesulfonylaminomethyl-2-methoxycarbonylbenzenesulfonamide (0.1 mol), 55 g of 4,6-dimethoxy-2-phenoxycarbonylaminopyrimidine (0.2 mol) and 100 mL of acetonitrile were added to the reaction In the device,After cooling to 0-5 ° C in an ice bath, 37 mL of 1,8-diazabicyclo [5.4.0] undec-7-ene (0.25 mol) was added and the mixture was reacted with 25 ° C for 2.5 h. After removing acetonitrile under reduced pressure, , The residue was added 100mL 2mol / L dilute hydrochloric acid and 100mL isopropyl ether,The solid was precipitated and filtered. The solid was washed with water and diisopropyl ether three times, respectively, and dried to obtain 44.2 g of mesosulfuron (10) in 88percent yield.
62%
With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 0 - 20℃; for 2 h;
Methyl 2-[(4,6-dimethoxypyrimidin-2-ylcarbamoyl)sulfamoyl]-α-(methanesulfonamido)-p-toluate (Example A6 in U.S. Pat. No. 5,648,315) 0.69 g (4.54 mmol) of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) was added at 0° C. to a suspension of 1.3 g (4.54 mmol) of 5-acetamidomethyl-2-methoxycarbonyl benzenesulfonamide and 1.25 g (4.54 mmol) of N-4,6-dimethoxypyrimidin-2-yl)phenylcarbamate in 20 ml of acetonitrile. After 2 hours at room temperature, the mixture was diluted with water and diethyl ether, acidified to pH 1-2 with hydrochloric acid, and the resulting precipitate was filtered off and dried. 1.32 g (62percent) of methyl 2-[(4,6-dimethoxypyrimidin-2-ylcarbamoyl)sulfamoyl]-α-(methanesulfonamido)-p-toluate having melting point of 149° C.-150° C. were obtained. As shown in , the X-ray powder diffraction pattern of the resulting mesosulfuron-methyl products prepared above has no significant signals, which indicates the mesosulfuron-methyl product prepared in accordance with the disclosure of U.S. Pat. No. 5,648,315 is amorphous.
Reference：
[1] Patent: CN106243046, 2016, A, . Location in patent: Paragraph 0047; 0069; 0070; 0089; 0090
[2] Patent: US2017/156332, 2017, A1, . Location in patent: Paragraph 0077
With triethylamine; In acetonitrile; at 60.0℃; for 0.166667h;Microwave irradiation;
A mixture of compound 6 (0.32 g, 1.16 mmol), compound 4 (0.25 g, 0.98 mmol) and triethylamine (0.12 g, 1.18 mmol) in acetonitrile (5 mL) was irradiated in a microwave at 60 C for 10 min. After completion of the reaction (checked by TLC), the reaction mixture was diluted with water (10 mL) and extracted with dichloromethane (10 mL). The organic layer was washed with 1 M HCl (2 × 5 mL) and then with water (20 mL) followed by brine solution (10 mL). The organic layer was dried over anhydrous sodium sulphate (6.2 g), filtered and evaporated under reduced pressure to obtain the crude product. The crude product was re-crystallized in acetonitrile (10 mL) to obtain the pure compound 7. Off-white powder; Yield: 0.410 g, 96 %; m.p.: 176 C (Lit. m.p.: 175.5-177.2 C); 1H NMR (400 MHz, CDCl3): delta 7.56 (s, 1H), 5.64 (s, 1H), 4.17 (s, 1H), 3.86 (s, 6H), 3.71 (s, 3H); ESI-MS: m/z,435.1 (M+1)+.
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