N-Iodosuccinimide → HCID 59447673, compound

HRID 1518273Notes

Reaction equation

HRID 1518273 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7]([O:9][CH3:10])=[O:8])[N:6]=1.C1C(=O)N([I:18])C(=O)C1>C(Cl)Cl.CCOC(C)=O>[NH2:1][C:2]1[S:3][C:4]([I:18])=[C:5]([C:7]([O:9][CH3:10])=[O:8])[N:6]=1

Participants

5

Reactant 2

HCID 120273N-IodosuccinimideHCID 840099Methyl 2-amino-1,3-thiazole-4-carboxylate

Product 1

HCID 59447673HCID 59447673, compoundYield 94.5%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of methyl 2-aminothiazole-4-carboxylate (5.6 g, 35.4 mmol) in DCM (60 mL) was added NIS (9.56 g, 42.5 mmol). The mixture was stirred at rt for 24 hours and then diluted with EtOAc (200 mL) and washed with water, brine, dried over Na2SO4, and concentrated under reduced pressure to provide 9.5 g (94%) of the desired product methyl 2-amino-5-iodothiazole-4-carboxylate (8A): LC/MS(APCI): m/z 284.9 (M+H).

Workup

  1. washwashed with water, brine
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ea89762248944c80abf7f8935dcb619b
Source dataset
uspto-grants-2012_07
Patent number
US08232273B2

Reaction notes

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