Diethyl (ethoxymethylene)malonate → HCID 7540596, compound

HRID 411189Notes

Reaction equation

HRID 411189 reaction equation
[NH2:1][C:2]1[S:3][C:4]([CH3:7])=[CH:5][N:6]=1.C([O:10][CH:11]=[C:12]([C:18](OCC)=O)[C:13]([O:15][CH2:16][CH3:17])=[O:14])C>C1(C)C(C)=CC=CC=1>[CH3:7][C:4]1[S:3][C:2]2=[N:1][CH:18]=[C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:11](=[O:10])[N:6]2[CH:5]=1

Participants

4

Reactant 2

HCID 6871Diethyl (ethoxymethylene)malonateHCID 3517702-Amino-5-methylthiazole

Product 1

HCID 7540596HCID 7540596, compoundYield 88.3%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A mixture of 2-amino-5-methyl thiazole (1.14 g) and diethyl ethoxymethylenemalonate (2.16 g) is heated at 135° C. in xylene (20 mL) for 2 h allowing for removal of the ethanol product. After the solvent is removed, the mixture is suspended in diphenyl ether (10 mL). The mixture is then heated to reflux with removal of ethanol for 30 min. The reaction mixture is cooled to rt and hexanes (20 mL) is added. The resulting precipitate is filtered, washed with diethyl ether (2×10 mL) and dried to afford 2.1 g (86%) of the title compound as a tan solid. Physical characteristics: 1H NMR (DMSO) δ 8.61, 8.05, 4.25, 2.48, 1.28; MS (ESI+) m/z 239 (M+H)+.

Workup

  1. customallowing for removal of the ethanol product
  2. customAfter the solvent is removed
  3. temperatureThe mixture is then heated
  4. temperatureto reflux with removal of ethanol for 30 min
  5. additionhexanes (20 mL) is added
  6. filtrationThe resulting precipitate is filtered
  7. washwashed with diethyl ether (2×10 mL)
  8. customdried

Sources & evidence

ORD record
ord-cb1cf2491156428b87630c6008d73730
Source dataset
uspto-grants-2003_05
Patent number
US06559145B2

Reaction notes

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