Diethyl (ethoxymethylene)malonate → HCID 22605696, compound

HRID 2307303Notes

Reaction equation

HRID 2307303 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([CH3:12])[C:6]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8].C(O[CH:16]=[C:17]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[C:18]([O:20][CH2:21][CH3:22])=[O:19])C>>[CH2:10]([O:9][C:7]([C:6]1[C:5]([CH3:12])=[CH:4][S:3][C:2]=1[NH:1][CH:16]=[C:17]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[C:23]([O:25][CH2:26][CH3:27])=[O:24])=[O:8])[CH3:11]

Participants

3

Reactant 2

HCID 6871Diethyl (ethoxymethylene)malonateHCID 521132Ethyl 2-amino-4-methylthiophene-3-carboxylate

Product 1

HCID 22605696HCID 22605696, compound

Conditions

Temperature
135 °C

Procedure

A mixture of ethyl 2-amino-4-methylthiophene-3-carboxylate (5.23 g) and diethyl ethoxymethylenemalonate (5.71 mL) is heated to 135° C. for 3 h with a stream of nitrogen passing through the flask. The mixture is allowed to cool to room temperature. The resulting solid is recrystallized (EtOH, 250 mL) to afford 9.23 g of the title compound as yellow needles. Physical characteristics. M.p. 126-128° C.; 1H NMR (400 MHz, DMSO-d6) δ12.36, 8.08, 6.77, 4.34, 4.24, 4.15, 2.31, 1.34, 1.27, 1.25; MS (ESI+) m/z 356 (M+H)+. Anal. Found: C, 54.12; H, 5.95; N, 3.99.; S, 8.99.

Workup

  1. temperatureto cool to room temperature
  2. customThe resulting solid is recrystallized (EtOH, 250 mL)

Sources & evidence

ORD record
ord-e8372d65829e47b9afdbbe8fd520562c
Source dataset
uspto-grants-2004_12
Patent number
US06831081B2

Reaction notes

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