Sodium Hydroxide → (2Z)-3-(2-Fluoro-5-methoxyphenyl)-2-mercapto-2-propenoic acid

HRID 2220297Notes

Reaction equation

HRID 2220297 reaction equation
[F:1][C:2]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][C:3]=1[CH:4]=[C:5]1[S:9]C(=S)N[C:6]1=[O:11].[OH-:18].[Na+]>>[F:1][C:2]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][C:3]=1/[CH:4]=[C:5](\[SH:9])/[C:6]([OH:18])=[O:11]

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 850594845-(2-Fluoro-5-methoxybenzylidene)-2-thioxo-1,3-thiazolidin-4-one

Product 1

HCID 58630707(2Z)-3-(2-Fluoro-5-methoxyphenyl)-2-mercapto-2-propenoic acidYield 100%

Procedure

5-(2-Fluoro-5-methoxybenzylidene)-2-thioxo-1,3-thiazolidin4-one (8.00 g, 9.7 mmol) was added in one portion to 25% w/v sodium hydroxide solution (40 mL). This was allowed stir at reflux for 1 h. After this time the reaction was allowed to cool to room temperature and poured onto water (50 mL). This was washed with dichloromethane (50 mL), and the aqueous layer acidified to pH 2 with aqueous hydrochloric acid (2 N, 50 mL) to give a white suspension. Product was extracted with ether (2×60 mL), dried (MgSO4) and solvent removed in vacuo to give a white solid (6.71 g, 100%); δH (300 MHz, CD3OD) 7.85 (1H, s, Ar), 7.46-7.35 (1H, m, Ar), 7.11 (1H, t, Ar), 7.01-6.75 (2H, m, CH═, and SH), 3.80 (3H, s, OCH3).

Workup

  1. temperatureat reflux for 1 h
  2. additionpoured onto water (50 mL)
  3. washThis was washed with dichloromethane (50 mL)
  4. customto give a white suspension
  5. extractionProduct was extracted with ether (2×60 mL)
  6. dry with materialdried (MgSO4) and solvent
  7. customremoved in vacuo

Sources & evidence

ORD record
ord-ab48041dd9a84391a8a6acc8df814282
Source dataset
uspto-grants-2008_08
Patent number
US07417064B2

Reaction notes

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