Diisopropyl Ether → HCID 19812269, compound

HRID 373431Notes

Reaction equation

HRID 373431 reaction equation
[C:1](#[N:5])[CH2:2][C:3]#[N:4].[N:6]([O-:8])=O.[Na+].Br[C:11]([CH3:18])([CH3:17])[C:12]([O:14][CH2:15][CH3:16])=[O:13].C(OC(C)C)(C)C>C(#N)C.O.C(O)(=O)C>[CH2:15]([O:14][C:12]([C:11]([CH3:18])([O:8][N:6]=[C:2]([C:1]#[N:5])[C:3]#[N:4])[CH3:17])=[O:13])[CH3:16]

Participants

8

Reactant 4

HCID 7914Diisopropyl EtherHCID 8010MalononitrileHCID 11745Propanoic acid, 2-bromo-2-methyl-, ethyl esterHCID 23668193Sodium Nitrite

Product 1

HCID 19812269HCID 19812269, compoundYield 100.6%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of malononitrile (300 g) and acetic acid (54.6 g) in acetonitrile (2.1 l) was added sodium nitrite (313 g) at 60°-65° C. After being stirred at the same temperature for an hour, ethyl 2-bromo-2-methylpropanoate (797 g) was added to the mixture at 65° C. After being refluxed for five hours, the mixture was cooled to the ambient temperature and allowed to stand overnight. The resulting mixture was poured into a mixture of water (4.2 l) and diisopropyl ether (4.2 l). The separated organic layer was washed with water and brine, dried over magnesium sulfate and evaporated under reduced pressure to give 2-(1-ethoxycarbonyl-1-methylethoxyimino)propanedinitrile (860 g).

Workup

  1. temperatureAfter being refluxed for five hours
  2. washThe separated organic layer was washed with water and brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-faf2b52053264cbca1be0574581c6cfc
Source dataset
uspto-grants-1992_11
Patent number
US05162520

Reaction notes

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