Hydrochloric Acid → N-(2-Chloro-4-fluorophenyl)-2-(hydroxyimino)-acetamide

HRID 844199Notes

Reaction equation

HRID 844199 reaction equation
Cl[C:2](Cl)(Cl)[CH:3]([OH:5])O.[OH2:8].O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+].[Cl:25][C:26]1[CH:32]=[C:31]([F:33])[CH:30]=[CH:29][C:27]=1[NH2:28].Cl.[NH2:35]O.Cl>O>[Cl:25][C:26]1[CH:32]=[C:31]([F:33])[CH:30]=[CH:29][C:27]=1[NH:28][C:3](=[O:5])[CH:2]=[N:35][OH:8]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 2707Chloral HydrateHCID 62649Sodium sulfate decahydrateHCID 75013Benzenamine, 2-chloro-4-fluoro-HCID 443297Hydroxyamine hydrochloride

Product 1

HCID 57368882N-(2-Chloro-4-fluorophenyl)-2-(hydroxyimino)-acetamideYield 75.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A solution of chloral hydrate (6.25 g, 37.8 mmol), sodium sulfate decahydrate (48.3 g, 340 mmol) and water (100 mL) was added to a stirred solution of 2-chloro-4-fluoroaniline (5.0 g, 34 mmol), hydroxylamine hydrochloride (9.19 g, 130 mmol), water (50 mL) and concentrated hydrochloric acid (3 mL). The reaction mixture was heated under reflux for 1 h, cooled to room temperature, stirred for 16 h and filtered. The filter-cake was recrystallised (methanol-water) to give the product (5.58 g, 75% yield) as a pale brown solid: IR νmax (Nujol)/cm−1 1655, 1613, 1536, 1267, 1191, 1021, 853 and 558; NMR δH (400 MHz, DMSO-d6) 7.20-7.29 (1H, m), 7.51-7.57 (1H, m), 7.78-7.84 (1H, m), 9.61 (1H, s) and 12.36 (1H, s).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 1 h
  3. filtrationfiltered
  4. customThe filter-cake was recrystallised (methanol-water)

Sources & evidence

ORD record
ord-774a251c8d6e491da70824cf728f482e
Source dataset
uspto-grants-2002_04
Patent number
US06380238B1

Reaction notes

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