Tert-Butyl nitrite → Ethyl 5-iodothiazole-4-carboxylate

HRID 2246071Notes

Reaction equation

HRID 2246071 reaction equation
N[C:2]1[S:3][C:4]([I:12])=[C:5]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[N:6]=1.C(ON=O)(C)(C)C>CN(C=O)C.[Cl-].[Na+].O>[CH2:10]([O:9][C:7]([C:5]1[N:6]=[CH:2][S:3][C:4]=1[I:12])=[O:8])[CH3:11]

Participants

5

Reactant 2

HCID 10906Tert-Butyl nitriteHCID 45117588Ethyl 2-amino-5-iodo-1,3-thiazole-4-carboxylate

Product 1

HCID 59705069Ethyl 5-iodothiazole-4-carboxylateYield 50.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A solution of 10.68 g of 2-amino-4-ethoxycarbonyl-5-iodothiazole in 140 ml of DMF was cooled in ice under an argon atmosphere. t-Butylnitrite (6.15 ml) was added to the cooled solution, and the mixture was stirred at room temperature for 30 min. The reaction solution was poured into brine, and the mixture was extracted three times with ethyl acetate. The organic layers were combined, followed by washing three times with brine. The organic layer was dried over anhydrous magnesium sulfate, was filtered, and was concentrated under the reduced pressure. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate=5:1 to 3:1) to give 5.08 g of 4-ethoxycarbonyl-5-iodothiazole.

Workup

  1. extractionthe mixture was extracted three times with ethyl acetate
  2. washby washing three times with brine
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. filtrationwas filtered
  5. concentrationwas concentrated under the reduced pressure
  6. customThe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=5:1 to 3:1)

Sources & evidence

ORD record
ord-66f8547db03d453d95e5c28d37c8bdf1
Source dataset
uspto-grants-2010_03
Patent number
US07687490B2

Reaction notes

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