Hydrochloric Acid → HCID 13286108, compound

Temperature

0 °C

To a suspension of 4.30 g (20.1 mmol, 1.0 equiv.) of 4-amino-N,N-dimethylbenzenemethanesulfonamide in 40 mL of concentrated aqueous hydrochloric acid and 20 mL of water cooled to 0° C. was added a solution of 1.38 g (20.1 mmol, 1.0 equiv.) of sodium nitrite in 20 mL of water dropwise. The reaction mixture became homogeneous during the addition. The reaction was stirred for fifteen minutes at 0° C. after the addition was complete. Meanwhile a solution of 22.6 g (100 mmol, 5.0 equiv.) of stannous chloride dihydrate in 40 mL of concentrated aqueous hydrochloric acid was prepared and cooled to -40° C. The solution of the diazonium salt was filtered into the stannous chloride solution. The reaction was allowed to warm to room temperature over the course of one hour. The reaction was then recooled to 0° C. and the precipitated product was collected by filtration. The solid was dried at 65° C. at 0.05 mm Hg for 45 minutes to yield 5.02 g (94%) of 4 -hydrazinyl-N,N-dimethylbenzenemethanesulfonamide hydrochloride.

1. additionThe reaction mixture became homogeneous during the addition
2. additionafter the addition
3. temperaturecooled to -40° C
4. filtrationThe solution of the diazonium salt was filtered into the stannous chloride solution
5. temperatureto warm to room temperature over the course of one hour
6. customwas then recooled to 0° C.
7. filtrationthe precipitated product was collected by filtration
8. customThe solid was dried at 65° C. at 0.05 mm Hg for 45 minutes

ORD record

ord-7c71ce0e0e134c9b81adb63c6161e647

Source dataset

uspto-grants-1994_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05300506