반응 #2381095

반응 방정식

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

수율 32.2%

용매

hexane

dichloromethane

dichloromethane

반응 조건

후처리

1. 1
   온도the mixture is refluxed for 13 hours
2. 2
   온도The solution is cooled to room temperature
3. 3
   온도cooling
4. 4
   추출the hydrochloric acid phase is extracted twice using dichloromethane
5. 5
   농축The 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
   여과filtered off with suction
9. 9
   workup.STIRRINGstirred for 15 minutes
10. 10
    여과the product is filtered off with suction
11. 11
    기타After drying in vacuo at 50° C.

실험 절차

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.

출처