Dimethylcarbamoyl Chloride → HCID 51354954, compound

Dimethylcarbamyl chloride (6.29 g, 58.4 mmol) was added slowly to 10.0 g (58.4 mmol) of N-octyl acetamide in 10 mL of dry toluene and the solution was refluxed under a nitrogen atmosphere for 16 h. The volatile materials were removed on a rotary evaporator and in vacuo. The residue, dissolved dichloromethane (30 mL), was stirred strongly for 30 min with a solution of 2.34 g (58.4 mmol) of sodium hydroxide in 40 mL of water. Calcium carbonate (2.34 g) was added to the mixture and it was stirred an additional 30 min. The organic phase was separated and the aqueous phase was washed with dichloromethane (30 mL×3). The combined organic phases were dried (calcium carbonate) and the volatile materials were removed on a rotary evaporator. The residue was distilled at 72-77° C./0.25 Torr to yield 7.1 g (61%) of product (purity 99% by GC). IR (neat) 2955, 2924, 2853 (C—H), 1627 (N═C) cm−1. 1H NMR 3.17 (t, 2H, JHH 6.9 Hz, —CH2—N═), 2.86 (s, 6H, —N—(CH3)2); 1.87 (s, 3H, —N═C(CH3)—N); 1.5 (m, 2H, —CH2—CH2—N═); 1.25-1.4 (m, 10H, CH3—(CH2)5—); 0.88 (t, 3H, JHH 6.1 Hz, CH3).

1. temperaturethe solution was refluxed under a nitrogen atmosphere for 16 h
2. customThe volatile materials were removed on a rotary evaporator and in vacuo
3. dissolutionThe residue, dissolved dichloromethane (30 mL)
4. customThe organic phase was separated
5. washthe aqueous phase was washed with dichloromethane (30 mL×3)
6. dry with materialThe combined organic phases were dried (calcium carbonate)
7. customthe volatile materials were removed on a rotary evaporator
8. distillationThe residue was distilled at 72-77° C./0.25 Torr

ORD record

ord-e70ad194f1204823a49edf5ebe530a5f

Source dataset

uspto-grants-2016_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09433895B2