Ethyl chloroformate → Ethyl (2,2-diethoxyethyl)carbamate

To a stirred solution of ethyl chloroformate (3 g, 0.027 mol.) and N-hydroxysuccinimide (3.8 g, 0.033 mol.) in 10 mL of DCM at 0° C. under nitrogen atmosphere was added N,N-Diisopropylethylamine (7.0 mL, 0.04 mol). The progress of the reaction was monitored by thin layer chromatography (TLC). After stirring for 3 hrs at room temperature. DCM was evaporated and the residue was dissolved in 10 mL of acetonitrile, cooled in an ice-bath and then added dropwise a solution of aminoacetaldehyde diethyl acetal (4.7 mL, 1.2 eq). The resulting mixture was stirred at ice-bath temperature for 1 h and then overnight at room temperature. The progress of the reaction was monitored by thin layer chromatography (TLC). The reaction mixture was filtered, and the precipitate was washed with 2×10 mL DCM and dried over sodium sulfate. After removing the solvent under reduce pressure, the residue was purified by silica gel column chromatography to give ethyl (2,2-diethoxyethyl)carbamate as a colorless oil

1. customDCM was evaporated
2. dissolutionthe residue was dissolved in 10 mL of acetonitrile
3. temperaturecooled in an ice-bath
4. stirringThe resulting mixture was stirred at ice-bath temperature for 1 h
5. customovernight
6. customat room temperature
7. filtrationThe reaction mixture was filtered
8. washthe precipitate was washed with 2×10 mL DCM
9. dry with materialdried over sodium sulfate
10. customAfter removing the solvent
11. customthe residue was purified by silica gel column chromatography

ORD record

ord-3371180f6be4499dad8458c6a950dfa0

Source dataset

uspto-grants-2016_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09296681B2