4-Toluenesulfonyl chloride → HCID 20335996, compound

To a stirred suspension of 7.9 g. (0.2 mole) of sodamide in 100 ml. of dry toluene was added 28.8 g. (0.2 mole) of 1,2-diethyl-4-pyrazolidinol at a rate so that a pot temperature of 30°-35° C. was maintained. After stirring 2.0 hrs. at room temperature, the solution was added dropwise to a solution of 38.0 g. (0.2 mole) of p-toluenesulfonyl chloride in 200 ml. of dry toluene with the pot temperature maintained below 30° C. After stirring for about one hr. at room temperature, the reaction mixture was washed twice with water and dried over sodium sulfate. The dried filtered solution was concentrated to a volume of about 100 ml., aniline (100 ml.) was added, the solution refluxed for 3.0 hrs. and then concentrated. The residue was partitioned between chloroform and dilute sodium hydroxide. The dried chloroform layer was concentrated and the residue distilled at 120° C./0.1 mm. to give 4.0 g. of product.

1. additionTo a stirred suspension of 7.9 g
2. additionat room temperature, the solution was added dropwise to a solution of 38.0 g
3. stirringAfter stirring for about one hr
4. washat room temperature, the reaction mixture was washed twice with water
5. dry with materialdried over sodium sulfate
6. filtrationThe dried filtered solution
7. concentrationwas concentrated to a volume of about 100 ml
8. addition, aniline (100 ml.) was added
9. temperaturethe solution refluxed for 3.0 hrs
10. concentrationand then concentrated
11. customThe residue was partitioned between chloroform and dilute sodium hydroxide
12. concentrationThe dried chloroform layer was concentrated
13. distillationthe residue distilled at 120° C./0.1 mm
14. customto give 4.0 g

ORD record

ord-03bdfc6bd8f1437081d4c3d8a3c027db

Source dataset

uspto-grants-1980_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04207327