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

HRID 1484618Notes

Reaction equation

HRID 1484618 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-ff80e0989fb244b4bcb2492f30de9c67
Source dataset
uspto-grants-2016_08
Patent number
US09422242B2

Reaction notes

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