Hydrochloric Acid → HCID 66749736, compound

HRID 537045Notes

Reaction equation

HRID 537045 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[O:12][C:11]([I:13])=[N:10][C:9]=1[C:14]([O:16]C)=[O:15].[OH-].[Na+].Cl>CCO.O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[O:12][C:11]([I:13])=[N:10][C:9]=1[C:14]([OH:16])=[O:15]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 66749494HCID 66749494, compound

Product 1

HCID 66749736HCID 66749736, compoundYield 62.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a stirred solution of methyl 5-(2-chlorophenyl)-2-iodo-1,3-oxazole-4-carboxylate (20.0 g, 55.2 mmol) in EtOH (300 mL) was added a solution of NaOH (3.3 g, 82.8 mmol) in water (100 mL). The reaction mixture was allowed to stir at rt overnight and was then acidified by the addition of 1M HCl. The solution was concentrated to a small volume and then extracted with EtOAc. The organic solutions were combined, dried over Na2SO4, filtered and concentrated to give 5-(2-chlorophenyl)-2-iodo-1,3-oxazole-4-carboxylic acid (12.0 g, 60%).

Workup

  1. concentrationThe solution was concentrated to a small volume
  2. extractionextracted with EtOAc
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-cd8f4934fd454ef3bc943c1bedad5ed2
Source dataset
uspto-grants-2014_10
Patent number
US08859768B2

Reaction notes

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