2-Mercaptobenzoic Acid → HCID 85590543, compound

HRID 1885295Notes

Reaction equation

HRID 1885295 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 were 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 were 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-8e382c1fb4a543a398decfd90c1fc30a
Source dataset
uspto-grants-1992_09
Patent number
US05143931

Reaction notes

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