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

HRID 1896560Notes

Reaction equation

HRID 1896560 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-af52485d0a124e6595e76e82fefaa9fb
Source dataset
uspto-grants-2013_08
Patent number
US08518970B2

Reaction notes

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