Acetic Acid → HCID 178432275, compound

HRID 2102403Notes

Reaction equation

HRID 2102403 reaction equation
[NH2:1][C:2]1[CH:6]=[CH:5][NH:4][N:3]=1.C([O:9][C:10](=O)[CH:11]([Cl:15])[C:12](=O)[CH3:13])C.C(O)(=O)C>CCO>[Cl:15][C:11]1[C:12]([CH3:13])=[N:1][C:2]2[N:3]([N:4]=[CH:5][CH:6]=2)[C:10]=1[OH:9]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 11858Ethyl 2-chloroacetoacetateHCID 178418806HCID 178418806, compound

Product 1

HCID 178432275HCID 178432275, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 3-aminopyrazole (10.0 g, 120.3 mmol), 2-chloro-3-oxo-butyric acid ethyl ester (16.7 mL, 120.3 mmol), and glacial acetic acid (103 mL) was heated to 120° C. for 1 hour. After cooling to room temperature, the reaction mixture was diluted with EtOH and concentrated. Trituration with Et2O gave 20.7 g (94%) desired product. MS APCI (+) m/z 184, 186 (M+, Cl pattern) detected; 1H NMR (400 mHz, CD3OD) δ 7.90 (d, 1H), 6.17 (d, 1H), 2.53 (s, 3H).

Workup

  1. temperatureAfter cooling to room temperature
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-022c944b7c9546d8b84121782a4761dd
Source dataset
uspto-grants-2009_08
Patent number
US07576072B2

Reaction notes

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