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

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).

1. additionOnce the addition
2. temperaturewas heated
3. temperatureat reflux for 2 minutes
4. filtrationThe resulting light brown precipitate was filtered
5. washwashed with H2O (200 mL)
6. customdried

ORD record

ord-62e3b4db55134910b92355b50077dc92

Source dataset

uspto-grants-2003_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06576656B1