Ammonium Acetate → HCID 86743945, compound

HRID 373432Notes

Reaction equation

HRID 373432 reaction equation
[C:1]([O-:4])(=[O:3])[CH3:2].[NH4+:5].[CH2:6]([O:8][C:9]([C:11]([CH3:20])([O:13][N:14]=[C:15]([C:18]#[N:19])[C:16]#[N:17])[CH3:12])=[O:10])[CH3:7].O.N>CO>[C:1]([OH:4])(=[O:3])[CH3:2].[C:18]([C:15](=[N:14][O:13][C:11]([C:9]([O:8][CH2:6][CH3:7])=[O:10])([CH3:12])[CH3:20])[C:16]([NH2:5])=[NH:17])#[N:19]

Participants

5

Reactant 3

HCID 517165Ammonium AcetateHCID 12896473Azane;hydrateHCID 19812269HCID 19812269, compound

Product 1

HCID 86743945HCID 86743945, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
20 °C

Procedure

To a solution of ammonium acetate (1258 g) in methanol (8.54 () were added 2-(1-ethoxycarbonyl-1-methylethoxyimino)propanedinitrile (854 g) and 28% ammonia water (568 ml). After the mixture was stirred at 20° C. for 15 hours, methanol was evaporated under reduced pressure. The residue was dissolved in a mixture of water (8 l) and tetrahydrofuran (8 l). After the aqueous layer was saturated with sodium chloride, the organic layer was separated and dried over magnesium sulfate. Acetic acid (368 g) was added to the solution, then the mixture was evaporated under reduced pressure, and the residue was triturated with diisopropyl ether (8 l) to give 2-cyano-2-(1-ethoxycarbonyl-1-methylethoxyimino)acetamidine acetate (689.1 g).

Workup

  1. custommethanol was evaporated under reduced pressure
  2. dissolutionThe residue was dissolved in a mixture of water (8 l) and tetrahydrofuran (8 l)
  3. customthe organic layer was separated
  4. dry with materialdried over magnesium sulfate
  5. additionAcetic acid (368 g) was added to the solution
  6. customthe mixture was evaporated under reduced pressure
  7. customthe residue was triturated with diisopropyl ether (8 l)

Sources & evidence

ORD record
ord-37ca33967ba64134be5d6d53363280b4
Source dataset
uspto-grants-1992_11
Patent number
US05162520

Reaction notes

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