Diethyl (ethoxymethylene)malonate → Diethyl 2-((2-bromo-4-cyanophenylamino)methylene)malonate

HRID 2367655Notes

Reaction equation

HRID 2367655 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[Br:10].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>C1(C)C=CC=CC=1>[Br:10][C:3]1[CH:4]=[C:5]([C:6]#[N:7])[CH:8]=[CH:9][C:2]=1[NH:1][CH:14]=[C:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:21]([O:23][CH2:24][CH3:25])=[O:22]

Participants

4

Reactant 2

HCID 6871Diethyl (ethoxymethylene)malonateHCID 15152794-Amino-3-bromobenzonitrile

Product 1

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

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 5.00 g (25.4 mmol) 4-amino-3-bromobenzonitrile in 30 mL of toluene was added 8.23 g (38.1 mmol) of diethyl ethoxymethylenemalonate (2a). The mixture was then heated to reflux for overnight with a condenser open to the air. The resulting solution was cooled down to room temperature and poured into 100 mL of hexanes. The white precipitate was collected and washed with hexanes (30 mL×3) to yield 11.9 g of an off-while solid as the desired product. MS ESI (m/z) 367 (M+1)+.

Workup

  1. temperatureThe mixture was then heated
  2. temperatureto reflux for overnight with a condenser open to the air
  3. customThe white precipitate was collected
  4. washwashed with hexanes (30 mL×3)

Sources & evidence

ORD record
ord-0c863126a77e479c910bf9f517aa3ca5
Source dataset
uspto-grants-2014_04
Patent number
US08697875B2

Reaction notes

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