Thiophenol → HCID 178526127, compound

HRID 621635

Reaction equation

HRID 621635 reaction equation
[OH-:1].[K+].[C:3]1([SH:9])[CH:8]=[CH:7][CH:6]=CC=1.Br[C:11]1[CH:19]=[CH:18][C:14]([C:15](O)=O)=[CH:13][CH:12]=1.CN(C)[C:22](=O)[CH3:23]>>[C:14]1([C:15]2[CH:6]=[CH:7][C:8]([C:3]([OH:1])=[S:9])=[CH:23][CH:22]=2)[CH:18]=[CH:19][CH:11]=[CH:12][CH:13]=1

Participants

5

Reactant 4

HCID 7969ThiophenolHCID 114644-Bromobenzoic acidHCID 14797Potassium HydroxideHCID 31374Dimethylacetamide

Product 1

HCID 178526127HCID 178526127, compound

Procedure

A solution of potassium hydroxide (20.86 g) in N,N-dimethylacetamide (70 ml) is heated to 150° C., and thereto are added with stirring thiophenol (19.52 ml) and 4-bromobenzoic acid (25.47 g) under nitrogen atmosphere at the same temperature. The mixture is refluxed under nitrogen atmosphere for 20 hours. The reaction mixture is poured into ice water (400 ml), and the mixture is washed with benzene (400 ml), and the aqueous layer is separated. The benzene layer is further extracted with 2.5N sodium hydroxide solution (100 ml×4). The extracts are combined with the above aqueous layer and adjusted to pH 1-2 with conc hydrochloric acid. The resulting precipitate is separated by filtration, washed with water and dried to give 4-phenylthiobenzoic acid (26.29 g).

Workup

  1. temperatureThe mixture is refluxed under nitrogen atmosphere for 20 hours
  2. washthe mixture is washed with benzene (400 ml)
  3. customthe aqueous layer is separated
  4. extractionThe benzene layer is further extracted with 2.5N sodium hydroxide solution (100 ml×4)
  5. customThe resulting precipitate is separated by filtration
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-1da58be216f4485eb0b7fc8eecf358ac
Source dataset
uspto-grants-1989_04
Patent number
US04824834

Linked notes

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