Diethyl Malonate → HCID 22054484, compound

HRID 1743921Notes

Reaction equation

HRID 1743921 reaction equation
[C:1]([O:9]CC)(=O)[CH2:2][C:3]([O:5]CC)=O.[I:12][C:13]1[CH:14]=[C:15]([CH:17]=[CH:18][C:19]=1[CH3:20])[NH2:16]>C(O)C>[I:12][C:13]1[CH:14]=[C:15]([NH:16][C:3](=[O:5])[CH2:2][C:1]([NH:16][C:15]2[CH:17]=[CH:18][C:19]([CH3:20])=[C:13]([I:12])[CH:14]=2)=[O:9])[CH:17]=[CH:18][C:19]=1[CH3:20]

Participants

4

Reactant 2

HCID 7761Diethyl MalonateHCID 1188893-Iodo-p-toluidine

Product 1

HCID 22054484HCID 22054484, compoundYield 81.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
210 °C

Procedure

A mixture of diethyl malonate (16.0 g, 100 mmol) and 3-iodo-4-methylaniline (46.6 g, 200 mmol) was heated at 210° C. for 20 min, allowing the liberated ethanol to evaporate. After cooling the solid formed was triturated in hot ethanol (200 mL) to afford the title compound (43.4 g, 81%). Light brown solid, ISP-MS: m/e=535.0 ([M+H]+).

Workup

  1. customto evaporate
  2. temperatureAfter cooling the solid
  3. customformed
  4. customwas triturated in hot ethanol (200 mL)

Sources & evidence

ORD record
ord-5cb28ba4605b44558e34df72a5ef5f6f
Source dataset
uspto-grants-2006_03
Patent number
US07012073B2

Reaction notes

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