Sodium Hydroxide → 4-Cyano-3-iodo-5-(methylsulfanyl)thiophene-2-carboxylic acid

HRID 2091682Notes

Reaction equation

HRID 2091682 reaction equation
[C:1]([C:3]1[C:4]([I:15])=[C:5]([C:10]([O:12]CC)=[O:11])[S:6][C:7]=1[S:8][CH3:9])#[N:2].[OH-].[Na+]>O1CCCC1.O>[C:1]([C:3]1[C:4]([I:15])=[C:5]([C:10]([OH:12])=[O:11])[S:6][C:7]=1[S:8][CH3:9])#[N:2]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 40152061Ethyl 4-cyano-3-iodo-5-(methylthio)thiophene-2-carboxylate

Product 1

HCID 580228624-Cyano-3-iodo-5-(methylsulfanyl)thiophene-2-carboxylic acidYield 80%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 4-cyano-3-iodo-5-(methylsulfanyl)thiophene-2-carboxylate (3.40 g, 10 mmol) in tetrahydrofuran (80 mL) and water (16 mL) was added a solution of 1.00M sodium hydroxide in water (30 mL). The solution was allowed to stir overnight. The reaction was quenched with a solution of 1N hydrogen chloride in water (50 mL) and diluted with water (400 mL). The resultant precipitate was filtered, washed with water (2×100 mL) and dried in a vacuum oven to give 4-cyano-3-iodo-5-(methylsulfanyl)thiophene-2-carboxylic acid (2.6 g, 79%) as a white solid. LCMS: (FA) ES+ 326. 1H NMR (400 MHz, d6-DMSO) δ: 14.1-13.8 (bs, 1H), 2.75 (s, 3H).

Workup

  1. customThe reaction was quenched with a solution of 1N hydrogen chloride in water (50 mL)
  2. additiondiluted with water (400 mL)
  3. filtrationThe resultant precipitate was filtered
  4. washwashed with water (2×100 mL)
  5. customdried in a vacuum oven

Sources & evidence

ORD record
ord-2f4aef9ef39547699a17f8baf8bb12c3
Source dataset
uspto-grants-2013_05
Patent number
US08440664B2

Reaction notes

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