Hydroxylamine → HCID 86608552, compound

HRID 2245809Notes

Reaction equation

C(OC(=O)/[CH:5]=[CH:6]/[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([S:13][C:14]2[CH:19]=[CH:18][C:17]([N:20]([CH3:22])[CH3:21])=[CH:16][CH:15]=2)[CH:8]=1)C.[NH2:24][OH:25].[OH-:26].[K+].[CH3:28]O>C1COCC1>[CH3:22][N:20]([CH3:21])[C:17]1[CH:16]=[CH:15][C:14]([S:13][C:9]2[CH:8]=[C:7]([C:6](=[CH2:5])[C:28]([NH:24][OH:25])=[O:26])[CH:12]=[CH:11][CH:10]=2)=[CH:19][CH:18]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of the (E)-3-(3-(4dimethylamino-phenylsulfanyl)-phenyl)-acrylic acid ethyl ester (327 mg, 1.0 mmol) in distilled THF (15 mL) containing 50% aqueous hydroxylamine (0.6 mL, 9.0 mmol) was added at 0° C. a solution of potassium hydroxide in methanol (1M, 1.6 mL, 1.6 mmol) in a dropwise manner. After stirring at 0° C. for 1 h, distilled water (15 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 (2×20 mL) and the combined extracts were washed with brine (20 mL), dried over anhydrous MgSO4, filtered and evaporated to dryness. The solid residue was recrystallised from ethanol to give the title compound (257 mg, 82%) as a yellow solid, mp 170° C. (decomp.).

Workup

distillationdistilled water (15 mL)
additionwas added
additionthe mixture was made neutral by dropwise addition of concentrated hydrochloric acid (10 M) at 0° C
extractionThe aqueous solution was extracted with ethyl acetate (2×20 mL)
washthe combined extracts were washed with brine (20 mL)
dry with materialdried over anhydrous MgSO4
filtrationfiltered
customevaporated to dryness
customThe solid residue was recrystallised from ethanol

Sources & evidence

ORD record: ord-a6f5bc6bde2045df97d5faa1c9521e7f
Source dataset: uspto-grants-2010_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07683185B2

Reaction notes

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