Hydroxylamine → HCID 85120026, compound

Temperature

0 °C

To a solution of 6-(4-dimethylamino-phenylsulfanyl)-hexa-2,4-dienoic acid methyl ester (0.556 g, 2.0 mmol) in distilled THF (10 mL) containing aqueous hydroxylamine (50%, 1.21 mL, 18.4 mmol) was added at 0° C. a solution of potassium hydroxide in methanol (1M, 2.8 mL, 2.8 mmol) over a period of 30 minutes. After stirring the mixture at 0° C. for an additional hour, distilled water (10 mL) was added and the mixture was made neutral by dropwise addition of concentrated hydrochloric acid (10 M) at 0° C. The solution was then extracted with ethyl acetate (2×50 mL), and the combined extracts were dried over anhydrous MgSO4, and evaporated to dryness. The solid residue was recrystallised from ethyl acetate to give the title compound (0.24 g, 43%) as a white solid.

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

ORD record

ord-a440af7e1ecb4d8fa3aee64f449a8f8a

Source dataset

uspto-grants-2010_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07683185B2