Ethanolamine → HCID 178438962, compound

To a solution of (2-isopropylphenyl)isothiocyanate (2.00 g) in diethylether (20 ml) was added 2-aminoethanol (0.69 g). The mixture was stirred at room temperature for 1 hour and concentrated under reduced pressure. To the obtained oil was added concentrated hydrochloric acid (5 ml). The mixture was refluxed for 3 hours. The reaction mixture was cooled to room temperature and poured into an aqueous solution of 20% sodium hydroxide (25 ml). The mixture was extracted with dichloromethane (60 ml), dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (n-hexane/ethyl acetate) to give 2-(2-isopropylphenyl)imino-1,3-thiazolidine (1.80 g, yield: 73%) as a white crystal. M.p. 76–77° C.

1. concentrationconcentrated under reduced pressure
2. additionTo the obtained oil was added concentrated hydrochloric acid (5 ml)
3. temperatureThe mixture was refluxed for 3 hours
4. temperatureThe reaction mixture was cooled to room temperature
5. additionpoured into an aqueous solution of 20% sodium hydroxide (25 ml)
6. extractionThe mixture was extracted with dichloromethane (60 ml)
7. dry with materialdried over anhydrous magnesium sulfate
8. concentrationconcentrated under reduced pressure
9. customThe obtained residue was purified by silica gel column chromatography (n-hexane/ethyl acetate)

ORD record

ord-fcce876fce794b4cb4af470cd41f1e9f

Source dataset

uspto-grants-2007_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07183275B2