Dimethylcarbamoyl Chloride → Ethanimidamide, N,N-dimethyl-N'-pentyl-

N-Hexyl acetamide (10.0 g, 77.5 mmol) was added 10 mL of dry toluene, then 8.33 g (77.5 mmol) of dimethylcarbamyl chloride was slowly added and then refluxed under a nitrogen atmosphere for 16 h. The volatile materials were removed on a rotary evaporator and then in vacuo at room temperature. The residue was dissolved dichloromethane (30 mL) and 3.1 g (77.5 mmol) of sodium hydroxide dissolved aqueous solution (40 mL) was added. The mixture was stirred vigorously for 30 min. Calcium carbonate (3.1 g) was added to the mixture and it was stirred another 30 min. The organic phase was separated and the aqueous phase was washed with dichloromethane (3×25 mL). The combined organic liquids were dried (calcium carbonate) and the volatile materials were removed on a rotary evaporator. The residue was distilled at 40-41° C./0.25 Torr to yield 4.7 g (39%) of product (98.5% pure by GC). IR (neat) 2956, 2927, 2857 (C—H), 1626 (N═C) cm−1. 1H NMR 3.18 (t, 2H, JHH 7.5 Hz, —CH2—N═), 2.87 (s, 6H, —N—(CH3)2); 1.88 (s, 3H, —N═C(CH3)—N); 1.51 (m, 2H, —CH2—CH2—N═); 1.25-1.4 (m, 4H, CH3—(CH2)2—); 0.90 (t, 3H, JHH 6.9 Hz, CH3). 13C NMR 158.90; 50.35; 38.15; 32.27; 29.98; 22.87; 14.31; 12.53.

1. temperaturerefluxed under a nitrogen atmosphere for 16 h
2. customThe volatile materials were removed on a rotary evaporator
3. customat room temperature
4. additionwas added
5. stirringwas stirred another 30 min
6. customThe organic phase was separated
7. washthe aqueous phase was washed with dichloromethane (3×25 mL)
8. dry with materialThe combined organic liquids were dried (calcium carbonate)
9. customthe volatile materials were removed on a rotary evaporator
10. distillationThe residue was distilled at 40-41° C./0.25 Torr

ORD record

ord-9ebe910c87e9471395cb08312d793359

Source dataset

uspto-grants-2016_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09433895B2