Sodium Hydroxide → HCID 42609111, compound

HRID 572615Notes

Reaction equation

HRID 572615 reaction equation
[C:1]([C:3]1[C:4]([I:18])=[C:5]([C:14]([O:16]C)=[O:15])[S:6][C:7]=1[N:8]1[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1)#[N:2].[OH-].[Na+]>C1COCC1.O>[C:1]([C:3]1[C:4]([I:18])=[C:5]([C:14]([OH:16])=[O:15])[S:6][C:7]=1[N:8]1[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1)#[N:2]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 68628672HCID 68628672, compound

Product 1

HCID 42609111HCID 42609111, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 4-cyano-3-iodo-5-morpholin-4-ylthiophene-2-carboxylate (1.5 g, 40.1 mmol) in THF (110 mL) was added a 1.0 M solution of sodium hydroxide in water (50 mL). The reaction mixture was allowed to stir at rt overnight and was then allowed to settle. The two layers were separated and the aqueous solution was washed with EtOAc and acidified with 1 N HCl. A precipitate formed and was filtered to give 4-cyano-3-iodo-5-morpholin-4-ylthiophene-2-carboxylic acid (1.2 g, 82%). LCMS: (FA) ES+ 365.0, ES− 363.1. 1H NMR (400 MHz, d6-DMSO) δ: 3.71-3.78 (m, 4H) and 3.51-3.58 (m, 4H).

Workup

  1. customThe two layers were separated
  2. washthe aqueous solution was washed with EtOAc
  3. customA precipitate formed
  4. filtrationwas filtered

Sources & evidence

ORD record
ord-bd6668ca52b341b196acd8143cfe826a
Source dataset
uspto-grants-2015_05
Patent number
US09029411B2

Reaction notes

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