Hydrochloric Acid → HCID 57445190, compound

HRID 2405839Notes

Reaction equation

HRID 2405839 reaction equation
C([O:3][C:4]([C:6]1[N:7]=[C:8]([NH:11][CH:12]([CH3:14])[CH3:13])[O:9][CH:10]=1)=[O:5])C.[OH-].[Na+].Cl>CCO.O>[CH:12]([NH:11][C:8]1[O:9][CH:10]=[C:6]([C:4]([OH:5])=[O:3])[N:7]=1)([CH3:14])[CH3:13]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 57445189HCID 57445189, compound

Product 1

HCID 57445190HCID 57445190, compoundYield 100.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To 2-isopropylamino-oxazole-4-carboxylic acid ethyl ester (2.5 g, 10.9 mmol) in EtOH (42 mL) and water (28 mL) was added NaOH (3.1 g, 77.4 mmol). The mixture was stirred at rt for 16 h, then cooled in an ice-bath and acidified to pH 3 with conc. HCl. The mixture was concentrated in vacuo to remove ethanol. The remaining aqueous phase was extracted with CH2Cl2 (3×200 mL). The organic phases were combined, dried over MgSO4 and concentrated to give 2-isopropylaminooxazole-4-carboxylic acid (1.86 g, 87% yield). LCMS found 171 [M+H]+.

Workup

  1. temperaturecooled in an ice-bath
  2. concentrationThe mixture was concentrated in vacuo
  3. customto remove ethanol
  4. extractionThe remaining aqueous phase was extracted with CH2Cl2 (3×200 mL)
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-f7ff55c2f32748a4b007de6e97385a94
Source dataset
uspto-grants-2014_08
Patent number
US08809267B2

Reaction notes

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