Diethylcarbamoyl chloride → N,N-dimethyl-2-[(diethylcarbamoyl)oxyimino]-3-methoxyiminobutyramide

HRID 26712

Reaction equation

HRID 26712 reaction equation
[CH3:1][N:2]([CH3:13])[C:3](=[O:12])[C:4](=[N:10][OH:11])[C:5](=[N:7][O:8][CH3:9])[CH3:6].[H-].[Na+].[H][H].[CH2:18]([N:20]([CH2:24][CH3:25])[C:21](Cl)=[O:22])[CH3:19]>O1CCCC1>[CH3:13][N:2]([CH3:1])[C:3](=[O:12])[C:4](=[N:10][O:11][C:21](=[O:22])[N:20]([CH2:24][CH3:25])[CH2:18][CH3:19])[C:5](=[N:7][O:8][CH3:9])[CH3:6]

Participants

6

Reactant 4

HCID 6916Diethylcarbamoyl chlorideHCID 24758Sodium hydrideHCID 136099002N,N-dimethyl-2-hydroxyimino-3-methoxyiminobutyramideHCID 178418361HCID 178418361, compound

Product 1

HCID 54436333N,N-dimethyl-2-[(diethylcarbamoyl)oxyimino]-3-methoxyiminobutyramide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred mixture of 75 parts of N,N-dimethyl-2-hydroxyimino-3-methoxyiminobutyramide and 1500 parts of tetrahydrofuran was added portionwise over a fifteen-minute period 19 parts of 50% sodium hydride, mineral oil dispersion. The temperature was maintained in the range of 20° C. to 30° C. After about one-half hour, evolution of hydrogen gas ceased, and rapid addition of 55 parts diethylcarbamoyl chloride was begun. The temperature spontaneously rose to 33° C., and rapid thinning-out of the oxime salt slurry occurred. The mixture was refluxed and stirred for three hours. The inorganic solids were then removed by filtration and the product recovered by removal of the solvent under reduced pressure. The residue was twice triturated with hexane and the liquid decanted to remove the mineral oil. After drying, there was obtained 90 parts of N,N-dimethyl-2-[(diethylcarbamoyl)oxyimino]-3-methoxyiminobutyramide, m.p. 59°-61°.

Workup

  1. temperatureThe temperature was maintained in the range of 20° C. to 30° C
  2. waitAfter about one-half hour
  3. customspontaneously rose to 33° C.
  4. temperatureThe mixture was refluxed
  5. customThe inorganic solids were then removed by filtration
  6. customthe product recovered by removal of the solvent under reduced pressure
  7. customThe residue was twice triturated with hexane
  8. customthe liquid decanted
  9. customto remove the mineral oil
  10. customAfter drying

Sources & evidence

ORD record
ord-a523c9ba4d524ffdbd3c37d2785780ee
Source dataset
uspto-grants-1979_04
Patent number
US04151296

Linked notes

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