反応 #2298457

反応方程式

trimethylaluminum

3-ethoxycarbonyl-2-iodobenzenesulfonamide

O-methyl (4-methyl-6-methoxy-1,3,5-triazin-2-yl)carbamate

hydrochloric acid

→

ethyl 2-iodo-3-[[[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)amino]carbonyl]amino]sulfonyl]-benzoate

収率 32.2%

溶媒

hexane

dichloromethane

dichloromethane

反応条件

後処理

1. 1
   温度the mixture is refluxed for 13 hours
2. 2
   温度The solution is cooled to room temperature
3. 3
   温度cooling
4. 4
   抽出the hydrochloric acid phase is extracted twice using dichloromethane
5. 5
   濃縮The organic phase is concentrated in vacuo
6. 6
   workup.ADDITIONthe residue is treated with acetone and 100 ml of 10% aqueous sodium acetate solution
7. 7
   workup.STIRRINGThe mixture is stirred for 3 hours
8. 8
   ろ過filtered off with suction
9. 9
   workup.STIRRINGstirred for 15 minutes
10. 10
    ろ過the product is filtered off with suction
11. 11
    その他After drying in vacuo at 50° C.

実験手順

14 mmol of trimethylaluminum (7 ml of a 2M solution in hexane) are added dropwise under a nitrogen protective atmosphere to a suspension of 3.6 g of 3-ethoxycarbonyl-2-iodobenzenesulfonamide in 100 ml of absolute dichloromethane. The mixture is stirred at room temperature for 30 minutes, and 2.2 g of O-methyl (4-methyl-6-methoxy-1,3,5-triazin-2-yl)carbamate in 25 ml of dichloromethane are then added, and the mixture is refluxed for 13 hours. The solution is cooled to room temperature, 25 ml of 2N hydrochloric acid are added dropwise with ice-cooling, and the hydrochloric acid phase is extracted twice using dichloromethane. The organic phase is concentrated in vacuo, and the residue is treated with acetone and 100 ml of 10% aqueous sodium acetate solution. The mixture is stirred for 3 hours and then filtered off with suction, followed by a washing step with diethyl ether, the aqueous phase is brought to pH 2-3 using concentrated hydrochloric acid and stirred for 15 minutes, and the product is filtered off with suction. After drying in vacuo at 50° C., 1.7 g of ethyl 2-iodo-3-[[[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)amino]carbonyl]amino]sulfonyl]-benzoate of m.p. 177°-9° C. are obtained.

出典