Toluene → HCID 23081195, compound

4-chlorobenzyl alcohol (3.00 g, 21.0 mmol) and triphosgene (3.12 g, 10.5 mmol) were dissolved in toluene (15 ml), to which N-ethyldiisopropylamine (3.6 ml, 21.0 mmol) was added while cooling in an ice-bath, and the mixture was stirred for 1 hour. The reaction mixture was poured into water, and extracted with methylene chloride twice. The extracts were combined and dried over magnesium sulfate, and then filtered. The filtrate was concentrated under a reduced pressure. A solution of 2-methallylamine hydrochloride (2.49 g, 23.1 mmol) in water (40 ml) were added to the residue, to which sodium carbonate (5.15 g, 48.6 mmol) was added under while cooling in an ice-bath, and the mixture was stirred for 15 minutes. The reaction mixture was extracted with methylene chloride twice, and the extracts were combined, dried over magnesium sulfate, and then filtered, and the filtrate was concentrated under a reduced pressure. The residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=10/1) to afford 4-chlorobenzyl N-(2-methyl-2-propenyl)carbamate (4.06 g, yield 80%) as a colorless liquid.

1. additionwas added
2. temperaturewhile cooling in an ice-bath
3. extractionextracted with methylene chloride twice
4. dry with materialdried over magnesium sulfate
5. filtrationfiltered
6. concentrationThe filtrate was concentrated under a reduced pressure
7. additionwas added under
8. temperaturewhile cooling in an ice-bath
9. stirringthe mixture was stirred for 15 minutes
10. extractionThe reaction mixture was extracted with methylene chloride twice
11. dry with materialdried over magnesium sulfate
12. filtrationfiltered
13. concentrationthe filtrate was concentrated under a reduced pressure
14. customThe residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=10/1)

ORD record

ord-66466e9cdce946a397c254469e0f2e95

Source dataset

uspto-grants-2007_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07262212B2