Malononitrile → HCID 71001839, compound

HRID 2274462Notes

Reaction equation

HRID 2274462 reaction equation
[C:1](#[N:5])[CH2:2][C:3]#[N:4].C(N(CC)CC)C.[CH2:13]([N:15]1[C:20]2[CH:21]=[C:22]([I:25])[CH:23]=[CH:24][C:19]=2[C:18](=O)[O:17]C1=O)[CH3:14]>CN(C=O)C>[NH2:4][C:3]1[N:15]([CH2:13][CH3:14])[C:20]2[C:19]([C:18](=[O:17])[C:2]=1[C:1]#[N:5])=[CH:24][CH:23]=[C:22]([I:25])[CH:21]=2

Participants

5

Reactant 3

HCID 8010MalononitrileHCID 8471Triethylamine2×HCID 71001847HCID 71001847, compound

Product 1

HCID 71001839HCID 71001839, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

0.32 g (6.31 mmol) of malononitrile and 1.45 g (14.35 mmol) triethylamine were added to 2 g (6.31 mmol) of 1-ethyl-7-iodo-1H-benzo[d][1,3]oxazine-2,4-dione dissolved in 25 mL of DMF. The solution was stirred for 2 hours at 120° C. and after addition of 0.73 g (7.17 mmol) of triethylamine, for another 1 hour at 110° C. The DMF was then evaporated under reduced pressure and the residue taken over with a mixture of water and dichloromethane. Filtration of this mixture gave a first fraction of the expected compound: 0.55 g (1.62 mmol).

Workup

  1. waitfor another 1 hour at 110° C
  2. customThe DMF was then evaporated under reduced pressure
  3. additionthe residue taken over with a mixture of water and dichloromethane
  4. filtrationFiltration of this mixture

Sources & evidence

ORD record
ord-18bd85c1152f4ff594657229cfe8ef5e
Source dataset
uspto-grants-2015_09
Patent number
US09126972B2

Reaction notes

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