Dimethylamine → 4-(Bromomethyl)-N,N-dimethylbenzenesulfonamide

4-(Bromomethyl)benzenesulfonyl chloride (5.0 g, 18.6 mmol) was dissolved in tetrahydrofuran. N,N-dimethylamine (7.7 mL, 15.5 mmol, 2M in tetrahydrofuran) and and N,N-diisopropylethylamine (3.5 mL, 20.1 mmol) were added, and the reaction was allowed to stir at ambient temperature for 2 hours. The reaction was concentrated to an oil that was partitioned between water and ethyl acetate and extracted with ethyl acetate. The organic extracts were combined, washed with brine, dried over Na2SO4, and filtered. The resulting filtrate was concentrated to an oil which deposited needles that were a mixture of the title compound and 4-chloromethyl N,N-dimethylbenzenesulfonamide. The resulting needles were collected. and dried (2.3 g, 44%). ES-MS m/z 534 (M+H) and 578 (M+H)

1. concentrationThe reaction was concentrated to an oil that
2. customwas partitioned between water and ethyl acetate
3. extractionextracted with ethyl acetate
4. washwashed with brine
5. dry with materialdried over Na2SO4
6. filtrationfiltered
7. concentrationThe resulting filtrate was concentrated to an oil which
8. additiona mixture of the title compound and 4-chloromethyl N,N-dimethylbenzenesulfonamide
9. customThe resulting needles were collected
10. customand dried (2.3 g, 44%)

ORD record

ord-69a2e418d170422991ff48ea24bbf7c8

Source dataset

uspto-grants-2006_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07067540B2