Hydrochloric Acid → HCID 13174436, compound

Temperature

4 °C

58.4 grams of N-cyclopropylcarbonyl-2,6-dichloroaniline was dissolved in 550 ml of anhydrous tetrahydrofuran under a nitrogen atmosphere in a 2 liter 3-necked flask. The mixture was cooled in an ice bath to 4° C. To this mixture was added 389 ml of 0.9 M-diboronhexahydride in anhydrous tetrahydrofuran over a period of one hour and ten minutes while maintaining a temperature of less than 5° C. After addition was complete, the solution was allowed to warm to room temperature and stirred for one hour. The solution was then heated to reflux and reflux was maintained overnight. The solution was then cooled in an ice bath and 225 ml 6 N aqueous hydrogen chloride was added. This mixture was then evaporated in vacuo to remove the tetrahydrofuran. The resultant liquid and solid residue was diluted with 500 ml of water and cooled in an ice bath. 75 g of sodium hydroxide in 300 ml of water was then added. The mixture was then extracted with ether and the ether extract was washed twice with 500 ml of water, 250 ml of saturated saline solution and dried over sodium sulfate. The resultant mixture was then filtered and the filtrate was evaporated in vacuo. The resultant oil was dissolved in 100 ml of methanol and acidified with 250 ml of methanol/hydrogen chloride and then evaporated in vacuo at 35°-40° C. The resultant oil residue was dissolved in 250 ml of isopropanol and a crystalline precipitate formed. The reaction yielded 33.0 g of white solid N-cyclopropyl methyl-2,6-dichloroaniline having a melting point of 149°-158° C.

1. temperatureten minutes while maintaining a temperature of less than 5° C
2. additionAfter addition
3. temperatureto warm to room temperature
4. temperatureThe solution was then heated
5. temperatureto reflux
6. temperaturereflux
7. temperaturewas maintained overnight
8. temperatureThe solution was then cooled in an ice bath
9. customThis mixture was then evaporated in vacuo
10. customto remove the tetrahydrofuran
11. additionThe resultant liquid and solid residue was diluted with 500 ml of water
12. temperaturecooled in an ice bath
13. addition75 g of sodium hydroxide in 300 ml of water was then added
14. extractionThe mixture was then extracted with ether
15. extractionthe ether extract
16. washwas washed twice with 500 ml of water, 250 ml of saturated saline solution
17. dry with materialdried over sodium sulfate
18. filtrationThe resultant mixture was then filtered
19. customthe filtrate was evaporated in vacuo
20. dissolutionThe resultant oil was dissolved in 100 ml of methanol
21. customevaporated in vacuo at 35°-40° C
22. dissolutionThe resultant oil residue was dissolved in 250 ml of isopropanol
23. customa crystalline precipitate formed

ORD record

ord-a0d920c2cca743fab87eaf7d121202f0

Source dataset

uspto-grants-1983_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04393077