2-Mercaptobenzoic Acid → HCID 85590543, compound

HRID 846194Notes

Reaction equation

HRID 846194 reaction equation
[C:1]([OH:10])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[SH:4].[S:11]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]Br)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[S:11]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][S:4][C:3]1[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=1[C:1]([OH:10])=[O:9])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 54432-Mercaptobenzoic AcidHCID 11430Potassium CarbonateHCID 10849841Benzene, [(6-bromohexyl)thio]-

Product 1

HCID 85590543HCID 85590543, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

Thiosalicylic acid (1.2 g, 0.008 mole) and 6-thio-phenoxyhexylbromide (2.5 g, 0.009 mole) are dissolved in dimethylformamide (50 ml) and the solution is stirred under argon. Potassium carbonate (1.5 g, 0.011 mole) is added carefully to the reaction. After the addition is complete the mixture is slowly warmed to 100° C. The solvents are evaporated, and the residue is dissolved in water, acidified with dilute hydrochloric acid, extracted with ethyl acetate, dried over anhydrous sodium sulfate, filtered, and evaporated. The residue is flash chromatographed on silica gel to give the desired product.

Workup

  1. additionAfter the addition
  2. customThe solvents are evaporated
  3. dissolutionthe residue is dissolved in water
  4. extractionextracted with ethyl acetate
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customchromatographed on silica gel

Sources & evidence

ORD record
ord-0eebb9c75f2c40409e1c93330a3b49a7
Source dataset
uspto-grants-1992_08
Patent number
US05135938

Reaction notes

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