2-Mercaptobenzoic Acid → HCID 59658526, compound

HRID 604966Notes

Reaction equation

HRID 604966 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:4].[C:11]([O-:14])([O-:13])=O.[K+].[K+].[SH:17][C:18]1[CH:26]=[CH:25][CH:24]=[CH:23][C:19]=1[C:20]([OH:22])=[O:21]>C(O)C>[C:11]([C:8]1[CH:9]=[CH:10][C:5]([C:3](=[O:4])[CH2:2][S:17][C:18]2[CH:26]=[CH:25][CH:24]=[CH:23][C:19]=2[C:20]([OH:22])=[O:21])=[CH:6][CH:7]=1)([OH:14])=[O:13]

Participants

5

Reactant 3

HCID 54432-Mercaptobenzoic AcidHCID 6259Phenacyl bromideHCID 11430Potassium Carbonate

Product 1

HCID 59658526HCID 59658526, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To bromoacetophenone (394.09 mg, 1.62 mmole) and anhydrous K2CO3 (896 mg, 6.48 mmole) in ethanol (20 ml), 250 mg (1.62 mmole) 2-mercaptobenzoic acid was added and the mixture refluxed overnight. The solvent was evaporated and water added to the solid residue. The aqueous layer was acidified to yield a precipitate which was filtered and dried (487 mg). m/z 315 (M−1)+. 1HNMR (DMSO) δ 4.75 (s, 2H, —CH2-), 7.22 (1H, t, ArH), 7.47 (2H, t, 2×ArH), 7.87 (1H, d, ArH), 8.06 (2H, d, 2×ArH), 8.15 (2H, d, 2×ArH).

Workup

  1. temperaturethe mixture refluxed overnight
  2. customThe solvent was evaporated
  3. additionwater added to the solid residue
  4. customto yield a precipitate which
  5. filtrationwas filtered
  6. customdried (487 mg)

Sources & evidence

ORD record
ord-800ac8dedc054c23b0a61ac0f66ae791
Source dataset
uspto-grants-2011_03
Patent number
US07910770B2

Reaction notes

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