Methyl 2-chloroacetoacetate → HCID 7454275, compound

HRID 2407720Notes

Reaction equation

HRID 2407720 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7](=[S:9])[NH2:8].Cl[CH:11]([C:16](=O)[CH3:17])[C:12]([O:14][CH3:15])=[O:13]>C(O)C>[CH3:17][C:16]1[N:8]=[C:7]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=2)[S:9][C:11]=1[C:12]([O:14][CH3:15])=[O:13]

Participants

4

Reactant 2

HCID 107332Methyl 2-chloroacetoacetateHCID 1549499Pyridine-2-carbothioamide

Product 1

HCID 7454275HCID 7454275, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
50 °C

Procedure

A mixture of pyridine-2-carbothioamide (5.00 g) and ethanol (15 mL) was heated at 50° C. Methyl 2-chloro-3-oxobutanoate (4.41 mL) was slowly added to this solution over 10 minutes. The solution was heated at 70° C. for 18 hours. The solution was cooled to room temperature and 50% ethanol (20 mL) was added. The solution was cooled to 0° C. and stirred for 1 hour. The solution was filtered and dried over vacuum to obtain the title compound (4.90 g) with the following physical data.

Workup

  1. temperatureThe solution was heated at 70° C. for 18 hours
  2. temperatureThe solution was cooled to room temperature
  3. temperatureThe solution was cooled to 0° C.
  4. filtrationThe solution was filtered
  5. customdried over vacuum

Sources & evidence

ORD record
ord-4ab2bce77349463b9531118c17eae95f
Source dataset
uspto-grants-2014_08
Patent number
US08809538B2

Reaction notes

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