Benzene → N,N-diallyl-N'-(chloroacetyl)-O-methylisourea

Temperature

10 °C

The isourea, 7.7 g (0.05 mole), was combined with 150 ml of tetrahydrofuran in a 500 ml three-neck flask. The solution was stirred and cooled in an ice-acetone bath to 10°C. Chloroacetyl chloride, 4 ml, 5.65 g (0.05 mole), was added drop-wise to the solution at such a rate that the temperature did not exceed 10°C. Following the addition, 69 ml, 5.05 g (0.05 mole) of triethyl amine was added drop-wise to the solution while the temperature was again maintained below 10°C. The resulting mixture was stirred at room temperature for 1 hour, then stirred for an additional hour at 45°C. The mixture was subsequently poured into 300 ml of benzene and washed with 150 ml of ice water. The organic phase was dried with MgSO4, and the solvent was evaporated to yield 10.4 g (90% yield) of N,N-diallyl-N'-(chloroacetyl)-O-methylisourea, nD30 1.4800, confirmed by NMR analysis.

1. customdid not exceed 10°C
2. additionwas added drop-wise to the solution while the temperature
3. customwas again maintained below 10°C
4. stirringThe resulting mixture was stirred at room temperature for 1 hour
5. stirringstirred for an additional hour at 45°C
6. washwashed with 150 ml of ice water
7. dry with materialThe organic phase was dried with MgSO4
8. customthe solvent was evaporated

ORD record

ord-5ff1453361e64afc9f95388c71017983

Source dataset

uspto-grants-1976_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US03984410