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Hydroxylamine → 6-(4'-Chloro-biphenyl-4-sulfinyl)-hexanoic acid hydroxyamide

HRID 2245798
Notes
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Reaction equation

HRID 2245798 reaction equation
C[O:2][C:3](=O)[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][S:9]([C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=2)=[CH:13][CH:12]=1)=[O:10].[NH2:25][OH:26].[OH-].[K+].CO>C1COCC1>[OH:26][NH:25][C:3](=[O:2])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][S:9]([C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=2)=[CH:13][CH:12]=1)=[O:10]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 787HydroxylamineHCID 887MethanolHCID 14797Potassium HydroxideHCID 100673776-(4'-Chloro-biphenyl-4-ylsulfinyl)-hexanoic acid methyl ester

Product 1

HCID 103167996-(4'-Chloro-biphenyl-4-sulfinyl)-hexanoic acid hydroxyamideYield 79%

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent

Conditions

Temperature
0 °C

Procedure

To a solution of the 6-(4′-chloro-biphenyl-4sulfinyl)-hexanoic acid methyl ester (400 mg, 1.1 mmol) in distilled THF (10 mL) containing 50% aqueous hydroxylamine (0.65 mL, 9.9 mmol) was added at 0° C. a solution of potassium hydroxide in methanol (1.9 mL, 1M, 1.9 mmol) in a dropwise manner. After stirring at 0° C. for 1 h, 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 aqueous solution was extracted with ethyl acetate (2×20 mL) and the combined extracts were washed with brine (40 mL), dried over anhydrous MgSO4, filtered and evaporated to dryness. The residue was recrystallised from acetone to give the title compound (315 mg, 79%) as a white powder, mp 108-110° C.

Workup

  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 aqueous solution was extracted with ethyl acetate (2×20 mL)
  5. washthe combined extracts were washed with brine (40 mL)
  6. dry with materialdried over anhydrous MgSO4
  7. filtrationfiltered
  8. customevaporated to dryness
  9. customThe residue was recrystallised from acetone

Sources & evidence

ORD record
ord-27d2117e8c0143989482d4f595f770cf
Source dataset
uspto-grants-2010_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07683185B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes