Sulfuric Acid → Bis-(3-chloroallyl)amine

N,N-Bis-(3-chloroallyl)cyanamide (38.2 g; 0.2 mole) was placed in a flask, and 16 milliliters (ml) of concentrated H2SO4 in 92 ml of water was added. The resulting mixture was refluxed for four hours under stirring, and then after the mixture was cooled to room temperature, 50 ml of water was added. The mixture was extracted with 50 ml of ether, and the ether extract was discarded. To the water phase, 200 ml of water was added. In an ice bath under stirring, a solution of 47.4 g of NaOH in 92 ml of water was slowly added dropwise. After the addition was completed, the mixture was extracted three times with ether; the ether phases were combined, washed with water twice, dried over magnesium sulfate, filtered and stripped. The yield was 85%. The product (28.2 g) was recovered as an orange-brown liquid.

1. temperatureThe resulting mixture was refluxed for four hours
2. extractionThe mixture was extracted with 50 ml of ether
3. extractionthe ether extract
4. additionTo the water phase, 200 ml of water was added
5. stirringIn an ice bath under stirring
6. additiona solution of 47.4 g of NaOH in 92 ml of water was slowly added dropwise
7. additionAfter the addition
8. extractionthe mixture was extracted three times with ether
9. washwashed with water twice
10. dry with materialdried over magnesium sulfate
11. filtrationfiltered
12. customThe product (28.2 g) was recovered as an orange-brown liquid

ORD record

ord-8f340cbc0ec9492cb93fa5c5f111118e

Source dataset

uspto-grants-1992_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05171356