Ethyl 2-aminothiazole-4-carboxylate → Ethyl 2-amino-5-iodo-1,3-thiazole-4-carboxylate

HRID 1799669Notes

Reaction equation

HRID 1799669 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[N:6]=1.[I:12]N1C(=O)CCC1=O>C1COCC1.[Cl-].[Na+].O>[NH2:1][C:2]1[S:3][C:4]([I:12])=[C:5]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[N:6]=1

Participants

5

Reactant 2

HCID 73216Ethyl 2-aminothiazole-4-carboxylateHCID 120273N-Iodosuccinimide

Product 1

HCID 45117588Ethyl 2-amino-5-iodo-1,3-thiazole-4-carboxylateYield 84%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A solution of 14.53 g of 2-amino-4-ethoxycarbonylthiazole in 200 ml of THF was cooled in ice under an argon atmosphere, 20.0 g of N-iodosuccinimide was added to the cooled solution, and the mixture was stirred at the same temperature for 1.5 hr. Brine was added to the reaction solution, and the mixture was extracted with ethyl acetate. 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=1:1 to 1:2) to give 21.12 g of 2-amino-4-ethoxycarbonyl-5-iodothiazole.

Workup

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

Sources & evidence

ORD record
ord-b38b169995ae4315973a4b8575b25c57
Source dataset
uspto-grants-2013_01
Patent number
US08344154B2

Reaction notes

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