FLORASULAM synthesis
- Product Name:FLORASULAM
- CAS Number:145701-23-1
- Molecular formula:C12H8F3N5O3S
- Molecular Weight:359.28
![[1,2,4]Triazolo[1,5-c]pyrimidine-2-sulfonyl chloride, 8-fluoro-5-methoxy-](/CAS/20200611/GIF/147150-78-5.gif)
147150-78-5
5509-65-9
145701-23-1
B. Add 5.1 g (40 mmol) of 2,6-difluoroaniline, 10 mL of alcohol solvent, and a small amount of naphthalene crystals (as an internal standard for liquid chromatography) to a 50 mL flask, and heat the mixture to 40 °C. Under nitrogen protection and stirring conditions, 2.67 g (10 mmol) of 2-chlorosulfonyl-8-fluoro-5-methoxy[1,2,4]triazolo[1,5-c]pyrimidine solid was slowly added until the chlorosulfonyl feedstock completely disappeared (monitored by high-pressure liquid chromatography). After completion of the reaction, the mixture was cooled to room temperature and the solid product was collected by filtration. The solid was washed with 10 mL of 2-propanol followed by water and dried. The resulting N-(2,6-difluorophenyl)-8-fluoro-5-methoxy-[1,2,4]triazolo[1,5-c]pyrimidine-2-sulfonamide was more than 99% pure (results are shown as Runs 4 through 6 in the table below).
147150-78-5
1 suppliers
inquiry
5509-65-9
496 suppliers
$10.00/10g
145701-23-1
198 suppliers
$63.00/250mg
Yield:145701-23-1 94.2%
Reaction Conditions:
Stage #1:2,6-difluoroaniline with N-chloro-succinimide;dimethylsulfide in acetonitrile at -20;Inert atmosphere;
Stage #2:2-chlorosulfonyl-8-fluoro-5-methoxy-[1,2,4]triazolo[1,5-c]pyrimidine with 3-Methylpyridine in acetonitrile at 20 - 40;Inert atmosphere;Temperature;
Steps:
1
Under nitrogen protection,Add to a 500mL four-neck reaction flask100mL of acetonitrile and 12.9g (0.1moL) of 2,6-difluoroaniline,Stir down to -20 ° C,A drop of dimethyl sulfide 3.1g (0.05moL),After dripping, stir for 30min.Then slowly dropwise add 26.67 g of N-chlorosuccinimide in acetonitrile solution.(Contains 6.67 g of N-chlorosuccinimide, 0.05 moL),After dropping, continue to react for 1 ~ 2h,Then slowly add 27.9g (0.3moL) of 3-methylpyridine,After stirring for 1h,56.6g of2-chlorosulfonyl-8-fluoro-5-methoxy [1,2,4] triazole[1,5-c] pyrimidine in acetonitrile(Containing 2-chlorosulfonyl-8-fluoro-5-methoxy[1,2,4] triazole [1,5-c] pyrimidine26.6g, 0.1moL) slowly added to the above reaction solution,Finished in 1h, then,Stir at room temperature for 1h,The temperature was increased to 40 ° C, and the reaction was performed for 3 to 4 hours.HPLC traced the 2,6-difluoroaniline content to <0.5% to end the reaction.After the reaction is over,Reduce the temperature of the reaction solution to below 0 ° C,Add 250 g of dilute acid water (containing 41.7 g of 35% by weight hydrochloric acid),Acidified to pH <2,Precipitation of a large amount of solids,Stir for 1h, suction filter,Filter cake washedRinse with a small amount of methanol, dry,33.8 g of diflusulfuron was obtained as a white powder,The yield was 94.2% and the purity was 98.5% (HPLC).
References:
Jiangsu Hao Harvest Weien Agrochemical Co., Ltd.;Gao Shiguang;Xue Huan;Cai Xuyang;Wu Tao;Xu Yuming;Tao Tao CN110563735, 2019, A Location in patent:Paragraph 0019-0032
57-55-6
1705 suppliers
$5.00/1g
147150-78-5
1 suppliers
inquiry
145701-23-1
198 suppliers
$63.00/250mg
1801-06-5
92 suppliers
$41.00/250mg
145701-23-1
198 suppliers
$63.00/250mg