Diethyl (ethoxymethylene)malonate → HCID 12807908, compound

HRID 1094665Notes

Reaction equation

HRID 1094665 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:9]=[CH:10][CH:11]=1)[NH2:8])([CH3:4])([CH3:3])[CH3:2].C([O:14][CH:15]=[C:16]([C:22](OCC)=O)[C:17]([O:19][CH2:20][CH3:21])=[O:18])C>>[C:1]([C:5]1[CH:6]=[C:7]2[C:9]([C:15](=[O:14])[C:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:22][NH:8]2)=[CH:10][CH:11]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 2

HCID 6871Diethyl (ethoxymethylene)malonateHCID 793343-tert-Butylaniline

Product 1

HCID 12807908HCID 12807908, compoundYield 47%

Conditions

Temperature
60 °C

Procedure

A mixture of 3-tert-butylaniline (5.30 g, 35.5 mmol) and diethyl ethoxymethylenemalonate (10.2 g, 47.30 mmol) were heated at 60° C. for 15 min. then 1 hour at 120° C. After the generated ethanol was evaporated in vacuo, the crude oil was added dropwise to boiling diphenylether (150 ml) at 200˜250° C. and the mixture was stirred at 250° C. for 90 min. After cooling to room temperature, the mixture was diluted with hexane (ca. 200 ml) and the precipitate solid was collected to give (4.55 g, 47%) of the title compound as a slightly yellow solid. The compound was used for the next step without the determination of NMR, MS for hard solids.

Workup

  1. custom1 hour
  2. customat 120° C
  3. customAfter the generated ethanol was evaporated in vacuo
  4. additionthe crude oil was added dropwise
  5. customat 200˜250° C.
  6. temperatureAfter cooling to room temperature
  7. additionthe mixture was diluted with hexane (ca. 200 ml)
  8. customthe precipitate solid was collected

Sources & evidence

ORD record
ord-92588517fa3140e3af509a1c72c1bacb
Source dataset
uspto-grants-2012_03
Patent number
US08134004B2

Reaction notes

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