Hexane → 5-Chloropentanoic acid (2-chloro-4,6-dimethylphenyl)amide

To a solution of 2-chloro-4,6-dimethylaniline (14.7 g) and diisopropylethylamine (18 mL) in 150 mL of THF, was added a solution of 5-chlorovaleryl chloride (12.2 mL) in 75 mL of THF. After the reaction mixture had been allowed to stir at room temperature overnight, it was filtered and the filtrate concentrated on the rotary evaporator. The residue was dissolved in ethyl acetate and washed with 1 M aqueous HCl, saturated aqueous sodium bicarbonate, and brine. The ethyl acetate solution was then dried with magnesium sulfate and concentrated on the rotary evaporator to give a solid which was combined with a 1:1 mixture of hexane and diethyl ether. After this mixture had been stirred for an hour, it was filtered and the collected solids were dried to provide 12.2 g of 5-chloropentanoic acid (2-chloro-4,6-dimethylphenyl)amide, mp 80.6–82.9° C.

1. filtrationit was filtered
2. concentrationthe filtrate concentrated on the rotary evaporator
3. dissolutionThe residue was dissolved in ethyl acetate
4. washwashed with 1 M aqueous HCl, saturated aqueous sodium bicarbonate, and brine
5. dry with materialThe ethyl acetate solution was then dried with magnesium sulfate
6. concentrationconcentrated on the rotary evaporator
7. customto give a solid which
8. stirringAfter this mixture had been stirred for an hour
9. filtrationit was filtered
10. customthe collected solids were dried

ORD record

ord-3a25beb5db0246c5b389d00d70de3f93

Source dataset

uspto-grants-2006_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07053103B2