Ethyl 2-chloroacetoacetate → HCID 178469277, compound

HRID 2244365Notes

Reaction equation

HRID 2244365 reaction equation
[CH3:1][NH:2][C:3](=S)[NH:4][NH2:5].[CH2:7]([O:9][C:10](=[O:16])[CH:11](Cl)[C:12]([CH3:14])=O)[CH3:8]>C1COCC1>[CH2:7]([O:9][C:10]([C:11]1[C:12]([CH3:14])=[N:5][NH:4][C:3]=1[NH:2][CH3:1])=[O:16])[CH3:8]

Participants

4

Reactant 2

HCID 11858Ethyl 2-chloroacetoacetateHCID 2723853N-Methylhydrazinecarbothioamide

Product 1

HCID 178469277HCID 178469277, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1 g of 4-methylthiosemicarbazide (9.51 mmol) and 1.565 g of ethyl-2-chloro-acetoacetate (9.51 mmol) in THF (20 ml) was stirred for 30 min at RT and then heated to reflux for 1 h. The yellow solid that precipitated was filtered off, washed with acetone and then dissolved in hot (95° C.) water. The precipitating sulfur was filtered off, the aqueous solution was cooled to 0° C., vigorously stirred and 5 ml of an aqueous ammonium hydroxide solution (25%) were added. A white precipitate formed and the suspension was stirred for an additional hour at RT. The precipitate was then filtered off and dried to give 1.04 g (60%) of 3-methyl-5-methylamino-1H-pyrazole-4-carboxylic acid ethyl ester as a white solid. MS (ISP) 184.1 (M+H)+.

Workup

  1. temperatureheated
  2. temperatureto reflux for 1 h
  3. filtrationThe yellow solid that precipitated was filtered off
  4. washwashed with acetone
  5. dissolutiondissolved in hot (95° C.) water
  6. filtrationThe precipitating sulfur was filtered off
  7. temperaturethe aqueous solution was cooled to 0° C.
  8. stirringvigorously stirred
  9. addition5 ml of an aqueous ammonium hydroxide solution (25%) were added
  10. customA white precipitate formed
  11. stirringthe suspension was stirred for an additional hour at RT
  12. filtrationThe precipitate was then filtered off
  13. customdried

Sources & evidence

ORD record
ord-4a7e3c7ccf344082b341d0dc3adb12b8
Source dataset
uspto-grants-2010_03
Patent number
US07678818B2

Reaction notes

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