Ethyl 2-(4-chlorobenzyl)acetoacetate → HCID 59179663, compound

HRID 2381866Notes

Reaction equation

HRID 2381866 reaction equation
[NH:1]([C:3]1[S:4][C:5]([C:9]([O:11][CH3:12])=[O:10])=[C:6]([CH3:8])[N:7]=1)[NH2:2].C([O:15][C:16](=O)[CH:17]([CH2:21][C:22]1[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=1)[C:18]([CH3:20])=O)C>C(O)C.O.C(O)(=O)C>[Cl:28][C:25]1[CH:24]=[CH:23][C:22]([CH2:21][C:17]2[C:16](=[O:15])[N:1]([C:3]3[S:4][C:5]([C:9]([O:11][CH3:12])=[O:10])=[C:6]([CH3:8])[N:7]=3)[NH:2][C:18]=2[CH3:20])=[CH:27][CH:26]=1

Participants

6

Reactant 2

HCID 2757404Ethyl 2-(4-chlorobenzyl)acetoacetateHCID 55281926HCID 55281926, compound

Product 1

HCID 59179663HCID 59179663, compoundYield 42%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of methyl 2-hydrazinyl-4-methylthiazole-5-carboxylate (0.25 g, 1.33 mmol) and 2-(4-chlorobenzyl)acetoacetic ethyl ester (0.24 g, 0.93 mmol) in ethanol (10 mL) and water (1 mL) was added 1 drop of acetic acid at ambient temperature. The reaction mixture was heated to reflux for 17 hours, cooled to ambient temperature. The precipitate was collected by filtration and titrated with ethyl ether to afford the title compound in 42% yield (0.22 g): 1H NMR (300 MHz, DMSO-d6) δ 7.27 (d, J=8.5 Hz, 2H), 7.21 (d, J=8.5 Hz, 2H), 3.78 (s, 3H), 3.52 (s, 2H), 2.58 (s, 3H), 2.14 (s, 3H); MS (ES+) m/z 378.1 (M+1).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 17 hours
  3. filtrationThe precipitate was collected by filtration

Sources & evidence

ORD record
ord-2c7300d118b048848d6a9e5f14d227ea
Source dataset
uspto-grants-2012_09
Patent number
US08258160B2

Reaction notes

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