Aniline → N-benzene sulfonyl phenyl cyanamide

To a 3 liter 3-necked flask equipped with a stirrer, addition funnel, thermometer, and drying tube was charged 93.1g (1.0 mole) of aniline, 111g (1.1 moles) of triethylene diamine and 250 ml. of tetrahydrofuran. To this reaction mixture was added dropwise a solution of 176.6g (1 mole) of benzenesulfonyl chloride in 300 ml. of tetrahydrofuran. The reaction mixture was stirred at room temperature for 2.5 hours and was then filtered. To the filtrate was added 111g of triethylene diamine and this solution was added dropwise to a solution of 87g (1.41 moles) of cyanogen chloride in 100 ml. of THF which was maintained at -5°C. with cooling, After this addition was complete the stirred reaction mixture was allowed to return to room temperature over a 161/2 hour period. The reaction mixture was filtered and the filament was added to water to precipitate the product. The product was recrystallized from aqueous methanol to yield 218g (84.7%) of N-benzene sulfonyl phenyl cyanamide, m.p. 65°-66°C.

1. customTo a 3 liter 3-necked flask equipped with a stirrer, addition funnel
2. customthermometer, and drying tube
3. filtrationwas then filtered
4. additionTo the filtrate was added 111g of triethylene diamine
5. temperaturewith cooling
6. additionAfter this addition
7. customthe stirred reaction mixture
8. customto return to room temperature over a 161
9. custom2 hour period
10. filtrationThe reaction mixture was filtered
11. additionthe filament was added to water
12. customto precipitate the product
13. customThe product was recrystallized from aqueous methanol

ORDレコード

ord-a1f50fa75fff408784ff0ffdab73c51f

出典データセット

uspto-grants-1976_03

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US03944526