Ethyl bromopyruvate → Ethyl 2-aminothiazole-4-carboxylate

HRID 1823943Notes

Reaction equation

HRID 1823943 reaction equation
Br[CH2:2][C:3](=O)[C:4]([O:6][CH2:7][CH3:8])=[O:5].[NH2:10][C:11]([NH2:13])=[S:12]>>[NH2:13][C:11]1[S:12][CH:2]=[C:3]([C:4]([O:6][CH2:7][CH3:8])=[O:5])[N:10]=1

Participants

3

Reactant 2

HCID 66144Ethyl bromopyruvateHCID 2723790Thiourea

Product 1

HCID 73216Ethyl 2-aminothiazole-4-carboxylateYield 152.6%

Conditions

Temperature
100 °C

Procedure

According to literature reference (Kelly, T. R.; Lang, F. J. Org. Chem. 1996, 61, 4623–4633), ethyl bromopyruvate (10.0 mL, 79.7 mmol) and thiourea (5.5 g, 72.3 mmol) are combined neat in a 100 mL flask and slowly heated to 100° C. over a 1 hour period. At approximately 70° C. a vigorous reaction occurs and the mixture becomes homogeneous. After reaching 100° C. the reaction is heated for an additional 20 minutes and then cooled to room temperature. Upon cooling the reaction product solidifies affording 19.0 grams of a crude ethyl 2-amino-4-thiazolecarboxylate which is used without further purification.

Workup

  1. customAt approximately 70° C. a vigorous reaction
  2. customAfter reaching 100° C.
  3. temperatureis heated for an additional 20 minutes
  4. temperaturecooled to room temperature
  5. temperatureUpon cooling the reaction product

Sources & evidence

ORD record
ord-3eb05492652942439a9c5e2b804ef4ec
Source dataset
uspto-grants-2006_05
Patent number
US07041690B2

Reaction notes

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