Ethyl cyanoacetate → HCID 23153938, compound

HRID 1175792Notes

Reaction equation

HRID 1175792 reaction equation
[C:1]([CH2:3]C(OCC)=O)#[N:2].[H-].[Na+].[CH3:11][O:12][C:13]1[CH:31]=[CH:30][C:16]([CH2:17][N:18]2[C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=3[C:21](=[O:28])O[C:19]2=[O:29])=[CH:15][CH:14]=1>CN(C)C(=O)C>[CH3:11][O:12][C:13]1[CH:14]=[CH:15][C:16]([CH2:17][N:18]2[C:23]3[C:22](=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:21](=[O:28])[CH:3]([C:1]#[N:2])[C:19]2=[O:29])=[CH:30][CH:31]=1

Participants

5

Reactant 3

HCID 7764Ethyl cyanoacetateHCID 24758Sodium hydrideHCID 4352988HCID 4352988, compound

Product 1

HCID 23153938HCID 23153938, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent2×

Conditions

Temperature
120 °C

Procedure

To a solution of ethyl cyanoacetate (7.9 ml) in N,N-dimethylacetamide (150 ml) was added sodium hydride (an oily, about 66%, 3.0 g), and added a solution of 1-(4-methoxybenzyl)2H-3,1-benzoxazine-2,4(1H)-dione (21.0 g) in N,N-dimethylacetamide (50 ml), stirred at 120° C. for 19 hours. After cooling, the reaction mixture was concentrated under reduced pressure. Water was added to the residue and the mixture was washed with ether. The aqueous layer was acidified by adding 1N hydrochloric acid. The precipitated solid was collected by filtration, washed with water, and dried to obtain the target compound (8.1 g).

Workup

  1. temperatureAfter cooling
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. additionWater was added to the residue
  4. washthe mixture was washed with ether
  5. additionby adding 1N hydrochloric acid
  6. filtrationThe precipitated solid was collected by filtration
  7. washwashed with water
  8. customdried

Sources & evidence

ORD record
ord-90af2adf8451451dbc877c51da7ad43d
Source dataset
uspto-grants-2010_11
Patent number
US07842701B2

Reaction notes

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