Hydrochloric Acid → Ethyl 2-chlorothiazole-4-carboxylate

HRID 1444256Notes

Reaction equation

HRID 1444256 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8](N)[S:9][CH:10]=1)=[O:5])[CH3:2].N([O-])=O.[Na+].[ClH:16]>O.Cl[Cu]>[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8]([Cl:16])[S:9][CH:10]=1)=[O:5])[CH3:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 73216Ethyl 2-aminothiazole-4-carboxylateHCID 23668193Sodium Nitrite

Product 1

HCID 13106141Ethyl 2-chlorothiazole-4-carboxylate

Reagents, catalysts & solvents 2

HCID 62652Cuprous chlorideCatalystHCID 962WaterSolvent2×

Procedure

The free based 2-amino-thiazole-4-carboxylic acid ethyl ester (306 mg, 1.78 mmol) and CuCl (238 mg, 2.4 mmol) were suspended in conc. HCl (8 ml) and the mixture cooled on a salt/ice bath. A pre-cooled solution of NaNO2 (166 mg, 2.4 mmol) in water (2 ml) was added over a period of 10 min. The mixture was allowed to warm to room temperature over 1 h and was stirred for a further 1 h. Water was added and the aqueous layer extracted with EtOAc (3×10 ml). The combined EtOAc layers were washed with brine, dried (Na2SO4), filtered and the solvent removed in vacuo to give the title compound.

Workup

  1. temperaturethe mixture cooled on a salt/ice bath
  2. extractionthe aqueous layer extracted with EtOAc (3×10 ml)
  3. washThe combined EtOAc layers were washed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-4daff204679d42fcb4230314aafe8ed7
Source dataset
uspto-grants-2010_02
Patent number
US07662839B2

Reaction notes

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