Ethanol → HCID 13253361, compound

HRID 1649037Notes

Reaction equation

HRID 1649037 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-f9de9230ce2e46079d78796d898e3074
Source dataset
uspto-grants-1983_11
Patent number
US04414388

Reaction notes

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