Dimethylformamide → HCID 137121553, compound

HRID 2166980Notes

Reaction equation

HRID 2166980 reaction equation
I[CH:2]([CH3:4])[CH3:3].CN(C)C=O.[NH2:10][C:11](=[N:17][OH:18])[C:12](=[N:15][OH:16])[C:13]#[N:14].C(=O)([O-])[O-].[K+].[K+]>O>[NH2:10][C:11](=[N:17][OH:18])[C:12](=[N:15][O:16][CH:2]([CH3:4])[CH3:3])[C:13]#[N:14]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6362Isopropyl iodideHCID 11430Potassium CarbonateHCID 137121577HCID 137121577, compound

Product 1

HCID 137121553HCID 137121553, compoundYield 53.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

2.52 g (14.8 mM) of 2-iodopropane was added to an N,N-dimethylformamide solution (30 ml) of 2.00 g (15.6 mM) of 3-amino-2,3-bis(hydroxyimino)propionitrile. The mixture was cooled to 0° C. 2.05 g (14.8 mM) of potassium carbonate was added, followed by stirring at room temperature for 16 hours. The reaction mixture was poured into water, followed by extraction with ethyl acetate. The organic layer obtained was washed with a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and filtered to remove inorganic matter. The solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography (ethyl acetete:hexane=1:2) to obtain 1.36 g (yield: 51%) of 3-amino-3-hydroxyimino-2-isopropoxyiminopropionitrile (compound No. 1-004).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. customThe organic layer obtained
  3. washwas washed with a saturated aqueous sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customto remove inorganic matter
  7. distillationThe solvent was distilled off under reduced pressure
  8. customThe resulting residue was purified by silica gel column chromatography (ethyl acetete:hexane=1:2)

Sources & evidence

ORD record
ord-a8b771bf94b64c8d94626ded1cc5fc9a
Source dataset
uspto-grants-2015_06
Patent number
US09044013B2

Reaction notes

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