Diiodomethane → 2-Iodo-thiazole-4-carboxylic acid ethyl ester

HRID 1799677Notes

Reaction equation

HRID 1799677 reaction equation
N(OC(C)(C)C)=O.I[CH2:9][I:10].NC1[S:13][CH:14]=[C:15]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[N:16]=1>C(#N)C.[Cl-].[Na+].O>[CH2:20]([O:19][C:17]([C:15]1[N:16]=[C:9]([I:10])[S:13][CH:14]=1)=[O:18])[CH3:21]

Participants

6

Reactant 3

HCID 6346DiiodomethaneHCID 10906Tert-Butyl nitriteHCID 73216Ethyl 2-aminothiazole-4-carboxylate

Product 1

HCID 684727782-Iodo-thiazole-4-carboxylic acid ethyl esterYield 65.8%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A solution of 6.0 ml of t-butyl nitrite in 120 ml of acetonitrile was cooled in ice under an argon atmosphere, and 9.64 g of diiodomethane and 5.16 g of 2-amino-4-ethoxycarbonylthiazole were added to the cooled solution. The mixture was stirred at room temperature for one hr, brine was added thereto, and the mixture was extracted twice with ethyl acetate. The organic layers were combined, were washed twice with brine, were dried over anhydrous magnesium sulfate, were filtered, and were 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 5.58 g of 4-ethoxycarbonyl-2-iodothiazole.

Workup

  1. extractionthe mixture was extracted twice with ethyl acetate
  2. washwere washed twice with brine
  3. dry with materialwere dried over anhydrous magnesium sulfate
  4. filtrationwere filtered
  5. concentrationwere 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-294a6934534948b2b289adeefa48dfdf
Source dataset
uspto-grants-2013_01
Patent number
US08344154B2

Reaction notes

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