Hydroxylamine → 6-(4-Dimethylaminophenylsulfinyl)hexanoic acid hydroxamide

Temperature

0 °C

To a solution of the 6-(4-dimethylamino-benzenesulfinyl)-hexanoic acid methyl ester (1.2 g, 4.0 mmol) in distilled THF (30 mL) containing 50% aqueous hydroxylamine (2.65 mL, 40 mmol) was added at 0° C. a solution of potassium hydroxide in methanol (6.8 mL, 1M, 6.8 mmol) in a dropwise manner. After stirring at 0° C. for 1 h, distilled water (30 mL) was added and the mixture was made neutral by dropwise addition of concentrated hydrochloric acid (10 M) at 0° C. The aqueous solution was extracted with ethyl acetate (3×50 mL) and the combined extracts were washed with brine (100 mL), dried over anhydrous MgSO4, filtered and evaporated to dryness. The solid residue was recrystallised from acetone to give the title compound (728 mg, 61%) as a white powder, mp 95-97° C.

1. distillationdistilled water (30 mL)
2. additionwas added
3. additionthe mixture was made neutral by dropwise addition of concentrated hydrochloric acid (10 M) at 0° C
4. extractionThe aqueous solution was extracted with ethyl acetate (3×50 mL)
5. washthe combined extracts were washed with brine (100 mL)
6. dry with materialdried over anhydrous MgSO4
7. filtrationfiltered
8. customevaporated to dryness
9. customThe solid residue was recrystallised from acetone

ORD record

ord-42898a06a45249aca04b631d4a735f6f

Source dataset

uspto-grants-2010_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07683185B2