Chlorobenzene → HCID 178512041, compound

Samples of 3-nitroaniline hydrochloride, 15.5 g, and 1-pyrrolidinecarbonitrile, 9.6 g, were combined with 12 ml of chlorobenzene, and the mixture was warmed to reflux for three hours, and then allowed to cool. The resulting solid mass was taken up in 200 ml of hot water, and the chlorobenzene layer was separated. The aqueous layer was washed with 30 ml of chloroform and the combined organic layers were washed with 50 ml of water. The aqueous layers were combined, warmed, treated with charcoal and filtered hot. The filtrate was allowed to cool, and made strongly basic with 50% sodium hydroxide. This basic mixture was extracted with 200 ml of chloroform. The chloroform extract was concentrated on a steam bath to 150 ml, then diluted with hexanes to 300 ml, and stirred until yellow solids formed, giving 17 g of the N-(3-nitrophenyl)-1-pyrrolidinecarboximidamide. m.p. 117-118° C.

1. temperaturethe mixture was warmed
2. temperatureto reflux for three hours
3. temperatureto cool
4. customthe chlorobenzene layer was separated
5. washThe aqueous layer was washed with 30 ml of chloroform
6. washthe combined organic layers were washed with 50 ml of water
7. temperaturewarmed
8. additiontreated with charcoal
9. filtrationfiltered hot
10. temperatureto cool
11. extractionThis basic mixture was extracted with 200 ml of chloroform
12. extractionThe chloroform extract
13. concentrationwas concentrated on a steam bath to 150 ml
14. additiondiluted with hexanes to 300 ml
15. customformed

ORD record

ord-d1f8d4c2b6574c249dd1b77c09d6c28a

Source dataset

uspto-grants-1999_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05998399