Ethanol → HCID 13253361, compound

HRID 905309Notes

Reaction equation

HRID 905309 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-e1b24691003f4468a2ca2ba6867719f6
Source dataset
uspto-grants-1983_12
Patent number
US04423048

Reaction notes

Loading…