Thionyl Chloride → HCID 18376600, compound

To a solution of N-(2-methyl-2-hydroxypropyl)-N′-ethylurea (7.2 g, 45 mmol) in CH2Cl2 (100 mL) at 0° C. was added a solution of thionyl chloride (5.4 g, 45 mmol) in CH2Cl2 (20 mL). The mixture was warmed to ambient temperature. After 2 hours, the mixture was concentrated in vacuo, and the resulting solid triturated with boiling water. The mixture was cooled to ambient temperature and made basic by addition of saturated aqueous K2CO3. The mixture was extracted with methylene chloride, dried over K2CO3, and concentrated in vacuo to afford 3.2 g (50% yield) of 2-ethylamino-5,5-dimethyloxazoline; NMR (DMSO-d6/TFA) 3.2 (s, 2), 3.0 (q, 2), 1.3 (s, 6), 1.0 (t, 3) ppm.

1. concentrationthe mixture was concentrated in vacuo
2. customthe resulting solid triturated with boiling water
3. temperatureThe mixture was cooled to ambient temperature
4. additionmade basic by addition of saturated aqueous K2CO3
5. extractionThe mixture was extracted with methylene chloride
6. dry with materialdried over K2CO3
7. concentrationconcentrated in vacuo

ORD record

ord-5f4bedec5eb04072825947f2958e4bd4

Source dataset

uspto-grants-2002_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06380221B1