Diethyl 2-((2-bromo-4-cyanophenylamino)methylene)malonate → HCID 178469455, compound

HRID 1484619Notes

Reaction equation

HRID 1484619 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([C:8]#[N:9])[CH:5]=[CH:4][C:3]=1[NH:10][CH:11]=[C:12]([C:18]([O:20]CC)=O)[C:13]([O:15][CH2:16][CH3:17])=[O:14]>C1(OC2C=CC=CC=2)C=CC=CC=1>[Br:1][C:2]1[CH:7]=[C:6]([C:8]#[N:9])[CH:5]=[C:4]2[C:3]=1[N:10]=[CH:11][C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:18]2[OH:20]

Participants

3

Reactant 1

HCID 66823182Diethyl 2-((2-bromo-4-cyanophenylamino)methylene)malonate

Product 1

HCID 178469455HCID 178469455, compoundYield 130.3%

Reagents, catalysts & solvents 1

HCID 7583Diphenyl EtherSolvent

Procedure

100 mL of diphenyl ether was heated to reflux followed by addition of 5.00 g (13.6 mmol) diethyl 2-((2-bromo-4-cyanophenylamino)methylene)malonate in portions in 30 minutes. The resulting brown solution was reflux for another hour and then cooled down to room temperature. The precipitate was collected and washed with hexanes (15 mL×3) to give 5.69 g of a light brown solid as the desired product. MS ESI (m/z) 321 (M+1)+.

Workup

  1. temperatureto reflux
  2. temperatureThe resulting brown solution was reflux for another hour
  3. customThe precipitate was collected
  4. washwashed with hexanes (15 mL×3)

Sources & evidence

ORD record
ord-4a850d876f1c4c0b83b30f9fda792ecd
Source dataset
uspto-grants-2016_08
Patent number
US09422242B2

Reaction notes

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