1-Bromo-3-chloropropane → HCID 11551084, compound

A mixture of N′-(2-cyano-5-hydroxy-4-methoxyphenyl)-N,N-dimethylimidoformamide (21.9 g, 66 mmol), caesium carbonate (998 g, 300 mmol) and 1-bromo-3-chloropropane (11 ml, 110 mmol) in acetonitrile (300 ml) was heated at reflux for 1 hour. The reaction mixture was cooled and the solvent evaporated in vacuo. Water (200 ml) was added and this was extracted with dichloromethane (2×150 ml). The organic solution was washed with brine (50 ml) and dried over magnesium sulphate. The solvent was evaporated in vacuo and the residue triturated with diethyl ether. The solid was collected by suction filtration and dried in vacuo to yield N′-(5-(3-chloropropoxy)-2-cyano-4-methoxyphenyl)-N,N-dimethylimidoformamide (17.7 g, 91% yield) as a white solid:

1. temperaturewas heated
2. temperatureat reflux for 1 hour
3. temperatureThe reaction mixture was cooled
4. customthe solvent evaporated in vacuo
5. additionWater (200 ml) was added
6. extractionthis was extracted with dichloromethane (2×150 ml)
7. washThe organic solution was washed with brine (50 ml)
8. dry with materialdried over magnesium sulphate
9. customThe solvent was evaporated in vacuo
10. customthe residue triturated with diethyl ether
11. filtrationThe solid was collected by suction filtration
12. customdried in vacuo

ORD record

ord-e8d8f20c29c649d4acfdcc35342f0a95

Source dataset

uspto-grants-2008_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07402585B2