Ammonia → {[(2R)-oxolan-2-yl]methyl}thiourea

To a 0° C. solution of (R)-(tetrahydrofuran-2-yl)methanamine (5.0 g, 49.5 mmol) and triethylamine (690 uL, 4.95 mmol) in tetrahydrofuran (100 mL) was added carbon disulfide (5.65 g, 74.3 mmol). Stirring was continued for 0.5 hour followed by the dropwise addition of 30% hydrogen peroxide (5.6 g, 49.5 mmol) so that the temperature was maintained below 40° C. The reaction mixture was poured into water, and extracted with ethyl acetate. The organic extract was dried (Na2SO4), filtered and concentrated to afford an oil. The residue was dissolved in tetrahydrofuran, and treated with 7 N ammonia in methanol (14.3 mL, 100 mmol). The precipitate was collected by filtration and washed with water to afford the title compound.

1. temperaturewas maintained below 40° C
2. extractionextracted with ethyl acetate
3. extractionThe organic extract
4. dry with materialwas dried (Na2SO4)
5. filtrationfiltered
6. concentrationconcentrated
7. customto afford an oil
8. filtrationThe precipitate was collected by filtration
9. washwashed with water

ORD record

ord-3649b802f1b549c09107e1811b046781

Source dataset

uspto-grants-2013_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08546583B2