Hydroxylamine → 6-(4-((4-Chlorobenzyl)-methylamino)-benzenesulfinyl)-hexanoic acid

HRID 2245797Notes

Reaction equation

HRID 2245797 reaction equation
C[O:2][C:3](=[O:27])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][S:9]([C:11]1[CH:16]=[CH:15][C:14]([N:17]([CH2:19][C:20]2[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=2)[CH3:18])=[CH:13][CH:12]=1)=[O:10].NO.[OH-].[K+].CO>C1COCC1>[Cl:26][C:23]1[CH:24]=[CH:25][C:20]([CH2:19][N:17]([CH3:18])[C:14]2[CH:13]=[CH:12][C:11]([S:9]([CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][C:3]([OH:27])=[O:2])=[O:10])=[CH:16][CH:15]=2)=[CH:21][CH:22]=1

Participants

6

Reactant 4

HCID 787HydroxylamineHCID 887MethanolHCID 14797Potassium HydroxideHCID 100470066-(4-((4-Chlorobenzyl)-methylamino)-benzenesulfinyl)-hexanoic acid methyl ester

Product 1

HCID 866085506-(4-((4-Chlorobenzyl)-methylamino)-benzenesulfinyl)-hexanoic acidYield 55%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of the 6-(4-((4-chlorobenzyl)-methylamino)-benzenesulfinyl)-hexanoic acid methyl ester (1.6 g, 4.0 mmol) in distilled THF (25 mL) containing 50% aqueous hydroxylamine (2.6 mL, 40 mmol) was added at 0° C. a solution of potassium hydroxide in methanol (1M, 8 mL, 8 mmol) in a dropwise manner. After stirring at 0° C. for 1 h, distilled water (25 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 (2×50 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/40-60° C. petroleum ether to give the title compound (867 mg, 53%) as a white powder, mp 109-111° C.

Workup

  1. distillationdistilled water (25 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 (2×50 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/40-60° C. petroleum ether

Sources & evidence

ORD record
ord-a9281f961dd64d17adfedd4b7f9af12d
Source dataset
uspto-grants-2010_03
Patent number
US07683185B2

Reaction notes

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