Sodium Hydroxide → HCID 22171376, compound

HRID 1866181Notes

Reaction equation

HRID 1866181 reaction equation
FC(F)(F)C([NH:5][CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([S:14][C:15]2[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=2)=[CH:10][CH:9]=1)=O.[OH-].[Na+]>CO>[NH2:5][CH2:6][CH2:7][C:8]1[CH:9]=[CH:10][C:11]([S:14][C:15]2[CH:16]=[CH:17][C:18]([OH:21])=[CH:19][CH:20]=2)=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 22171265HCID 22171265, compound

Product 1

HCID 22171376HCID 22171376, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2,2,2-trifluoro-N-[2-[4-[(4-hydroxyphenyl)thio]phenyl]ethyl]acetamide (480 mg) in methanol (5.0 ml) was added 1N sodium hydroxide solution (2.8 ml). The mixture was refluxed for 12 hours. The mixture was evaporated under reduced pressure. The residue was dissolved in a mixture of dichloromethane (40 ml), 1N hydrochloric acid solution (2.0 ml) and water (15 ml). After separation, the organic layer was dried over magnesium sulfate and evaporated under reduced pressure to give 4-[[4-(2-aminoethyl)phenyl]thio]phenol (300 mg).

Workup

  1. temperatureThe mixture was refluxed for 12 hours
  2. customThe mixture was evaporated under reduced pressure
  3. dissolutionThe residue was dissolved in a mixture of dichloromethane (40 ml), 1N hydrochloric acid solution (2.0 ml) and water (15 ml)
  4. customAfter separation
  5. dry with materialthe organic layer was dried over magnesium sulfate
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-6ab3ea21b4b84329bfee8f2e7d4a0142
Source dataset
uspto-grants-2009_12
Patent number
US07629366B2

Reaction notes

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