Potassium Carbonate → HCID 58168556, compound

HRID 1255253Notes

Reaction equation

HRID 1255253 reaction equation
[SH:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6].C(=O)([O-])[O-].[K+].[K+].Br[CH2:18][CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21]>CN(C=O)C>[CH2:23]([O:22][C:20](=[O:21])[CH2:19][CH2:18][S:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6])[CH3:24]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 68320Ethyl 3-bromopropionateHCID 95737Benzoic acid, 3-mercapto-

Product 1

HCID 58168556HCID 58168556, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 3-mercaptobenzoic acid (3.4 g) in DMF (50 mL) was treated with potassium carbonate (3.18 g) and stirred for 5 minutes. A solution of ethyl 3-bromopropionate (2.8 mL) in DMF (10 mL) was added dropwise over 30 minutes and the resulting mixture was stirred for a further 30 minutes. The mixture was partitioned between ethyl acetate and water, and the phases separated. The aqueous phase was acidified with aqueous HCl and extracted further with ethyl acetate. The organic phases were washed with water, dried, filtered and concentrated under reduced pressure to afford the subtitled compound. Yield 5.3 g.

Workup

  1. stirringthe resulting mixture was stirred for a further 30 minutes
  2. customThe mixture was partitioned between ethyl acetate and water
  3. customthe phases separated
  4. extractionextracted further with ethyl acetate
  5. washThe organic phases were washed with water
  6. customdried
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-dac66115d47d4198951cde9d985e820b
Source dataset
uspto-grants-2013_06
Patent number
US08455483B2

Reaction notes

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