Benzene → HCID 178526127, compound

HRID 37148

Reaction equation

HRID 37148 reaction equation
CN(C)C(=O)C.C1([SH:13])C=CC=CC=1.Br[C:15]1[CH:23]=[CH:22][C:18]([C:19]([OH:21])=O)=[CH:17][CH:16]=1.[CH:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>[OH-].[K+]>[C:24]1([C:15]2[CH:16]=[CH:17][C:18]([C:19]([OH:21])=[S:13])=[CH:22][CH:23]=2)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

6

Reactant 4

HCID 241BenzeneHCID 7969ThiophenolHCID 114644-Bromobenzoic acidHCID 31374Dimethylacetamide

Product 1

HCID 178526127HCID 178526127, compound

Reagents, catalysts & solvents 1

HCID 14797Potassium HydroxideSolvent

Conditions

Temperature
150 °C

Procedure

A solution of 70 ml of N,N-dimethylacetamide in which 20.86 g of potassium hydroxide was dissolved was heated to 150° C., and 19.52 ml of thiophenol and 25.47 g of 4-bromobenzoic acid were added under nitrogen atmosphere while stirring at the same temperature. After reflux for 20 hours under nitrogen atmosphere, the reaction mixture was poured into 400 ml of ice water, and 400 ml of benzene was added to wash, and the water layer was separated. The benzene layer was extracted with 2.5N sodium hydroxide (100 ml×4). The extract was combined with the water layer and the pH was adjusted to 1 to 2 with concentrated hydrochloric acid, and the precipitate was filtered, washed in water, dried, and 4-phenylthiobenzoic acid was obtained (26.29 g).

Workup

  1. temperatureAfter reflux for 20 hours under nitrogen atmosphere
  2. additionwas added
  3. washto wash
  4. customthe water layer was separated
  5. extractionThe benzene layer was extracted with 2.5N sodium hydroxide (100 ml×4)
  6. filtrationthe precipitate was filtered
  7. washwashed in water
  8. customdried

Sources & evidence

ORD record
ord-3b002c86051440ea974d1ecc49654d6f
Source dataset
uspto-grants-1995_05
Patent number
US05420128

Linked notes

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