Chlorosuccinimide → Ethyl 2-amino-5-chloro-1,3-thiazole-4-carboxylate

HRID 1641048Notes

Reaction equation

HRID 1641048 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.[Cl:12]N1C(=O)CCC1=O>C(#N)C.CCOC(C)=O>[NH2:1][C:2]1[S:3][C:4]([Cl:12])=[C:5]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[N:6]=1

Participants

5

Reactant 2

HCID 31398ChlorosuccinimideHCID 73216Ethyl 2-aminothiazole-4-carboxylate

Product 1

HCID 21780304Ethyl 2-amino-5-chloro-1,3-thiazole-4-carboxylateYield 98.4%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

Ethyl 2-aminothiazole-4-carboxylate (4.72 g, 27.4 mmol) was combined with N-chlorosuccinimide (4.0 g, 30 mmol) and dissolved in acetonitrile (50 mL). The mixture was heated at mild reflux (>81.5° C.) for 5 hours. Subsequently, the flask was cooled to rt and decolorizing carbon was added to the mixture which was further diluted with EtOAc. The resulting slurry was filtered through a pad of silica and concentrated under reduced pressure to provide 5.57 g (98%) of the desired product ethyl 2-amino-5-chlorothiazole-4-carboxylate (1H). The analytical data on this compound corresponded to that previously reported (see, South, M. S. J. Heterocyclic Chem. 1991, 28, 1003.).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat mild reflux (>81.5° C.) for 5 hours
  3. additionwas added to the mixture which
  4. filtrationThe resulting slurry was filtered through a pad of silica
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1d51027296b64bdba70c3425ed37bac9
Source dataset
uspto-grants-2012_02
Patent number
US08114893B2

Reaction notes

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