Sodium Hydroxide → 2-Sulfanyl-3-[5-(trifluoromethyl)furan-2-yl]prop-2-enoic acid

HRID 1863472Notes

Reaction equation

HRID 1863472 reaction equation
[F:1][C:2]([F:17])([F:16])[C:3]1[O:7][C:6]([CH:8]=[C:9]2[S:13]C(=S)N[C:10]2=[O:15])=[CH:5][CH:4]=1.[OH-:18].[Na+]>O>[SH:13][C:9](=[CH:8][C:6]1[O:7][C:3]([C:2]([F:17])([F:16])[F:1])=[CH:4][CH:5]=1)[C:10]([OH:18])=[O:15]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 538729252-Sulfanylidene-5-{[5-(trifluoromethyl)furan-2-yl]methylidene}-1,3-thiazolidin-4-one

Product 1

HCID 713702922-Sulfanyl-3-[5-(trifluoromethyl)furan-2-yl]prop-2-enoic acidYield 60%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1.58 g of the above 5-(5-trifluoromethyl-2-furylmethylene)rhodanine, 23 ml of 1 N sodium hydroxide solution and 25 ml of water are stirred under nitrogen at room temperature for 10 hours. After cooling with an ice bath and acidification with concentrated hydrochloric acid to pH 1.5, the resulting slurry is filtered to yield a slightly brown precipitate which is washed with 50 ml of water by stirring at room temperature under nitrogen and filtered to yield 0.8 g of slightly brown crystals (yield 60%) of α-mercapto-β-(5-trifluoromethyl-2-furyl)acrylic acid, M.P. 158° C.

Workup

  1. temperatureAfter cooling with an ice bath
  2. filtrationacidification with concentrated hydrochloric acid to pH 1.5, the resulting slurry is filtered
  3. customto yield a slightly brown precipitate which
  4. washis washed with 50 ml of water
  5. filtrationfiltered

Sources & evidence

ORD record
ord-15365698b06446469f800ab47a701135
Source dataset
uspto-grants-1979_09
Patent number
US04169149

Reaction notes

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