Hydrochloric Acid → 4-Sulfamoylbenzene-1-sulfonyl chloride

温度

0 °C

To the 700 ml Erlenmeyer flask was taken up 54 ml of the distilled water and 72 ml of the concentrated hydrochloric acid. The solution was cooled to 0° C. and 24 g (0.139 mol) of sulfanilamide III was added successively portionwise under stirring. The mixture was stirred at this temperature another 1 hour. To this mixture, the solution of 9.6 g (0.139 mol) of sodium nitrite in 16 ml of the water was added dropwise for 30 minutes under stirring and cooling, so as the temperature of the mixture does not exceed 0° C. The mixture was then stirred another 30 minutes at the 0° C. In the meantime, the solution of 36 g (0.56 mol) of sulphur dioxide in 120 ml of 99% acetic acid was prepared. Sulphur dioxide was prepared by the successive addition of 100 g of sodium pyrosulphite to 250 ml 40% sulphuric acid. Prepared sulphur dioxide was taken up under cooling to the 120 ml of 99% acetic acid at +5° C. until the weight gain reaches 36 g. To this solution, 1.4 g of copper dichloride dihydrate was added and the mixture was stirred. To this mixture, the solution of prepared diazonium salt it is then added for 5 minutes under gentle stirring for 10 minutes in three portions so as the temperature of the mixture did not exceed +5° C. After about 15 min evolution of forming nitrogen occurs. The mixture was stirred another 15 min, 200 ml of the mixture of the water and the grinded ice was added and the mixture was stirred another 20 min. Obtained solid was separated, washed 3 times with the ice water and dried. Crystallization from ethyl acetate. Colourless solid m.p. 156-157° C. Afforded 14.9 g (42%) of 4-sulfamoylbenzenesulphonyl chloride V.

1. stirringThe mixture was stirred at this temperature another 1 hour
2. stirringunder stirring
3. temperaturecooling, so as the temperature of the mixture
4. customdoes not exceed 0° C
5. stirringThe mixture was then stirred another 30 minutes at the 0° C
6. stirringthe mixture was stirred
7. stirringunder gentle stirring for 10 minutes in three portions so as the temperature of the mixture
8. customdid not exceed +5° C
9. stirringThe mixture was stirred another 15 min
10. stirringthe mixture was stirred another 20 min
11. customObtained solid
12. customwas separated
13. washwashed 3 times with the ice water
14. customdried
15. customCrystallization from ethyl acetate

ORDレコード

ord-5575f43bdd7249f1ae16a786bae7f96b

出典データセット

uspto-grants-2012_06

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08193184B2