2-Aminothiazole → HCID 14920282, compound

HRID 918882Notes

Reaction equation

HRID 918882 reaction equation
CO[CH:3]=[C:4]([C:11]([O:13][CH3:14])=[O:12])[CH:5]=[CH:6][C:7]([O:9]C)=O.[NH2:15][C:16]1[S:17][CH:18]=[CH:19][N:20]=1>CN(C=O)C>[O:9]=[C:7]1[N:15]([C:16]2[S:17][CH:18]=[CH:19][N:20]=2)[CH:3]=[C:4]([C:11]([O:13][CH3:14])=[O:12])[CH:5]=[CH:6]1

Participants

4

Reactant 2

HCID 21552-AminothiazoleHCID 71338068Dimethyl 4-(methoxymethylidene)pent-2-enedioate

Product 1

HCID 14920282HCID 14920282, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

After 2 g (9.9 mmol) of dimethyl 4-(methoxymethylene)2-pentenedioate obtained in Example 1-1 was dissolved in 10 mL of DMF, 1 g (9.9 mmol) of 2-aminothiazole was added to the solution. Afterward, the resulting reaction solution was stirred under reflux at about 150° C. for 6 hours. After termination of the reaction was determined by liquid chromatography, the solvent was removed in vacuo and was then washed using brine, followed by drying using magnesium sulfate, and filtration. After distillation under reduced pressure, the resulting product was purified using column chromatography (hexane:ethylacetate=1:3) to obtain a target compound (Actual yield: 1 g, Percent yield: 43%).

Workup

  1. customAfterward, the resulting reaction solution
  2. customthe solvent was removed in vacuo
  3. washwas then washed
  4. customby drying
  5. filtrationmagnesium sulfate, and filtration
  6. distillationAfter distillation under reduced pressure
  7. customthe resulting product was purified
  8. customto obtain a target compound (Actual yield: 1 g, Percent yield: 43%)

Sources & evidence

ORD record
ord-f38f9f6d475a4f5bae6ec4edbfe84b24
Source dataset
uspto-grants-2016_03
Patent number
US09271976B2

Reaction notes

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