2-Mercaptobenzoic Acid → HCID 20083426, compound

HRID 344715Notes

Reaction equation

HRID 344715 reaction equation
[C:1]([OH:10])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[SH:4].[H-].[Na+].Br[CH2:14][CH2:15][CH2:16][Cl:17].C(=O)(O)[O-].[Na+]>CN(C)C=O>[Cl:17][CH2:16][CH2:15][CH2:14][S:4][C:3]1[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=1[C:1]([OH:10])=[O:9]

Participants

6

Reactant 4

HCID 54432-Mercaptobenzoic AcidHCID 80061-Bromo-3-chloropropaneHCID 24758Sodium hydrideHCID 516892Sodium Bicarbonate

Product 1

HCID 20083426HCID 20083426, compoundYield 39.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

With stirring at room temperature, 15.4 g (99.9 mmols) of thiosalicylic acid was added by small portions to 50 ml of a solution of 2.44 g (101.7 mmols) of sodium hydride in dimethylformamide. The solution was dropwise added to 100 ml of a solution of 15.7 g (99.7 mmols) of 1-bromo-3-chloropropane in dimethylformamide with stirring under ice cooling. The mixture was stirred under ice cooling for further an hour and a half. After the reaction, an aqueous saturated sodium bicarbonate solution was added to the mixture followed by extraction of the solution with ethyl acetate 10 times. The ethyl acetate layer was dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: chloroform/methanol =50/1) to afford 9.0 g (yield: 39%) of 1-chloro-3-(2-hydroxycarbonylphenylthio)propane.

Workup

  1. stirringwith stirring under ice cooling
  2. stirringThe mixture was stirred under ice cooling for further an hour
  3. customAfter the reaction
  4. extractionfollowed by extraction of the solution with ethyl acetate 10 times
  5. dry with materialThe ethyl acetate layer was dried over anhydrous sodium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (eluent: chloroform/methanol =50/1)

Sources & evidence

ORD record
ord-2efce416343b4993b1d764d44499ffc0
Source dataset
uspto-grants-1991_10
Patent number
US05053408

Reaction notes

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