Hydroxyamine hydrochloride → N-[(2,4-dichloro-1,3-thiazol-5-yl)methylidene]hydroxylamine

HRID 1584025Notes

Reaction equation

HRID 1584025 reaction equation
Cl.[NH2:2][OH:3].[Cl:4][C:5]1[S:6][C:7]([CH:11]=O)=[C:8]([Cl:10])[N:9]=1.C(=O)(O)[O-].[Na+]>C(O)C.O>[Cl:4][C:5]1[S:6][C:7]([CH:11]=[N:2][OH:3])=[C:8]([Cl:10])[N:9]=1

Participants

6

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 14886722,4-Dichloro-1,3-thiazole-5-carboxaldehyde

Product 1

HCID 2778786N-[(2,4-dichloro-1,3-thiazol-5-yl)methylidene]hydroxylamineYield 99%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

First 153 g (2.2 mol) of hydroxylamine hydrochloride in portions, then a solution of 364 g (2 mol) of 2,4-dichloro-5-thiazolecarboxaldehyde (II) in 1 liter of ethanol are added to a solution of 185 g (2.2 mol) of sodium bicarbonate in 5 liters of water at room temperature, with stirring. A voluminous, colourless precipitate separates out after 1 to 2 minutes. After stirring for 1 hour, the solid is filtered off with suction, washed with water and dried. 390 g (=99% of theory) of 2,4-dichloro-5-thiazolecarboxaldehyde oxime (IV) of melting point about 160° C. are obtained. It can be dehydrated to give the nitrile without further purification.

Workup

  1. stirringAfter stirring for 1 hour
  2. filtrationthe solid is filtered off with suction
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-850e7a4834c34d218b58c255fcd44d36
Source dataset
uspto-grants-1985_11
Patent number
US04555577

Reaction notes

Loading…