Chloral → Acetamide, 2-(hydroxyimino)-N-phenyl-

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To a solution of trichloroacetaldehyde monohydate (13.25 g, 1.3 eq) in H2O (150 mL) was successively added sodium sulfate (17.55 g, 4.0 eq), a hot solution (ca. 80° C.) of 3,5-dichloroaniline (10.0 g, 61.5 mmol) in H2O (50 mL) and 37% HCl (6.1 mL), and a solution of hydroxylamine hydrochloride (16.3 g, 3.8 eq) in H2O (75 mL) with rapid stirring. Once the addition was completed the reaction mixture was heated at reflux for 2 minutes and then allowed to cool to room temperature. The resulting light brown precipitate was filtered, washed with H2O (200 mL) and then dried to yield the crude isonitrosoacetanilide (20.13 g).

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