[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]
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°.
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