4-Methoxybenzenesulfonyl chloride → 4-Methoxybenzenesulfonamide

Temperature

70 °C

With stirring 96.47 g (0.467 m) of the 4-methoxybenzenesulfonyl chloride obtained in part A above was slowly added to a slurry of 175.0 ml of concentrated ammonium hydroxide and 175.0 g of ice keeping the temperature under -5° C. during the addition. Slowly the resulting mixture was heated to approximately 70° C. over approximately two and one half hours. The resulting slurry was cooled and maintained at approximately 10° C. for about forty minutes. The solid was collected by filtration, washed three times with 50.0 ml of ice water and dried on the filter to obtain 97.37 g of water-wet 4-methoxybenzenesulfonamide. This product was suspended in 664.0 ml of water and 22.0 ml of 50 percent aqueous sodium hydroxide and 3.75 g of decolorizing carbon was added. After approximately forty-five minutes, the carbon was collected by filtration and washed twice with 50.0 ml of water. The filtrate and 50.0 ml or rinse water was adjusted to approximately pH 3 with the addition of approximately 33.0 ml of concentrated hydrochloric acid. The resulting slurry was cooled to approximately 5° C., stirred approximately two hours and the solid was collected by filtration, washed three times each with 50.0 ml of ice water and dried in vacuo to obtain 70.93 g of 4-methoxybenzenesulfonamide, a shiny white solid which melted at 111.5°-112.50° C. The nuclear magnetic resonance spectrum was concordant with the assisgned structure.

1. customobtained in part
2. additionduring the addition
3. temperatureThe resulting slurry was cooled
4. temperaturemaintained at approximately 10° C. for about forty minutes
5. filtrationThe solid was collected by filtration
6. washwashed three times with 50.0 ml of ice water
7. customdried on the
8. filtrationfilter
9. customto obtain 97.37 g of water-wet 4-methoxybenzenesulfonamide
10. waitAfter approximately forty-five minutes
11. filtrationthe carbon was collected by filtration
12. washwashed twice with 50.0 ml of water
13. washThe filtrate and 50.0 ml or rinse water
14. additionwas adjusted to approximately pH 3 with the addition of approximately 33.0 ml of concentrated hydrochloric acid
15. temperatureThe resulting slurry was cooled to approximately 5° C.
16. filtrationthe solid was collected by filtration
17. washwashed three times each with 50.0 ml of ice water
18. customdried in vacuo

ORD record

ord-584b3d3185c44cf9a51d4b4d4359ca4a

Source dataset

uspto-grants-1989_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04874894