Ethanol → HCID 13253361, compound

HRID 485131Notes

Reaction equation

HRID 485131 reaction equation
Cl.[CH2:2]([C:4]1[N:5]=[C:6](CC)[S:7][CH:8]=1)[CH3:3].C(O[CH:14]=[C:15]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:16]([O:18][CH2:19][CH3:20])=[O:17])C.C([N:28](CC)CC)C.[CH2:33](O)[CH3:34]>C(OCC)(=O)C.O>[C:21]([C:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:14][NH:28][C:6]1[S:7][C:8]([CH2:33][CH3:34])=[C:4]([CH2:2][CH3:3])[N:5]=1)([O:23][CH2:24][CH3:25])=[O:22]

Participants

7

Reactant 4

HCID 702EthanolHCID 6871Diethyl (ethoxymethylene)malonateHCID 8471TriethylamineHCID 20271258HCID 20271258, compound

Product 1

HCID 13253361HCID 13253361, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

Diethylthiazole hydrochloride (15.4 g., 80 mmoles), diethyl ethoxymethylenemalonate (19.0 g., 88 mmoles), triethylamine (8.1 g., 80 mmoles) and ethanol (125 ml.) were combined and refluxed for 2.5 hours. The reaction mixture was cooled and stripped of solvent. The resulting semisolid product was distributed between ethyl acetate and water. The 2-(2,2-dicarbethoxyethenylamino)-4,5-diethylthiazole (28.6 g.) was obtained as a golden oil from the ethyl acetate phase by drying over anhydrous sodium sulfate and stripping.

Workup

  1. temperaturerefluxed for 2.5 hours
  2. temperatureThe reaction mixture was cooled

Sources & evidence

ORD record
ord-c8c189c894934da5b7e01ef64611e20d
Source dataset
uspto-grants-1985_08
Patent number
US04535081

Reaction notes

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