Acetic Acid → 2-Methoxyimino-2-cyanoacetamide

反応式

[C:1]([CH2:3][C:4]([NH2:6])=[O:5])#[N:2].[N:7]([O-:9])=O.[Na+].[C:11](O)(=O)C.[OH-].[Na+].S(OC)(OC)(=O)=O>O>[C:1]([C:3](=[N:7][O:9][CH3:11])[C:4]([NH2:6])=[O:5])#[N:2]

参加物

反応物 5

HCID 176Acetic Acid

HCID 6497Dimethyl Sulfate

HCID 7898Cyanoacetamide

HCID 14798Sodium Hydroxide2 回

HCID 23668193Sodium Nitrite

生成物 1

HCID 534247972-Methoxyimino-2-cyanoacetamide収率 77%

試薬・触媒・溶媒 1

実験手順

To a stirred mixture of α-cyanoacetamide (252 g, 3 mole) and sodium nitrite (414 g, 6 mole) in water (600 ml) was added acetic acid (371 ml, 10 mole) at 5°-10° C. over 1.5 hours. The mixture was allowed to stir for another 1.5 hours and adjusted to pH 8.5 with 6N NaOH. To the mixture was added dimethyl sulfate (568 ml, 6 mole) at 15°-20° C. and the mixture was stirred at 45° C. for 1.5 hours. The reaction mixture was adjusted to pH 8.5 with 6N NaOH and allowed to stand at 5° C. overnight to separate the precipitate, which was collected by filtration, washed with cold water and air-dried to give 292 g (77%) of the title compound as brown needles melting at 170°-172° C.