Hydroxylamine → 6-(4Dimethylamino-phenylsulfanyl)hexanoic acid

HRID 2245786Notes

Reaction equation

HRID 2245786 reaction equation
C[O:2][C:3](=[O:19])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][S:9][C:10]1[CH:15]=[CH:14][C:13]([N:16]([CH3:18])[CH3:17])=[CH:12][CH:11]=1.NO.[OH-].[K+].CO>C1COCC1>[CH3:18][N:16]([CH3:17])[C:13]1[CH:12]=[CH:11][C:10]([S:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][C:3]([OH:19])=[O:2])=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 787HydroxylamineHCID 887MethanolHCID 14797Potassium HydroxideHCID 10401484HCID 10401484, compound

Product 1

HCID 866085476-(4Dimethylamino-phenylsulfanyl)hexanoic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 6-(4-dimethylamino-phenylsulfanyl)-hexanoic acid methyl ester (722 mg, 2.6 mmol) in distilled THF (20 mL) containing 50% aqueous hydroxylamine (1.7 mL, 25.7 mmol) was added at 0° C. a solution of potassium hydroxide in methanol (1M, 4.4 mL, 4.4 mmol) in a dropwise manner. After stirring at 0° C. for 1 h, distilled water (20 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 (2×40 mL) and the combined extracts were washed with brine (80 mL), dried over anhydrous MgSO4, filtered and evaporated to dryness. The title compound was obtained as a colourless oil (377 mg, 52%).

Workup

  1. distillationdistilled water (20 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 (2×40 mL)
  5. washthe combined extracts were washed with brine (80 mL)
  6. dry with materialdried over anhydrous MgSO4
  7. filtrationfiltered
  8. customevaporated to dryness

Sources & evidence

ORD record
ord-95246bf5cdec4df5aeb2921949fd5a32
Source dataset
uspto-grants-2010_03
Patent number
US07683185B2

Reaction notes

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