Hydroxyamine hydrochloride → 4-amino-2,6-dichloro-N'-hydroxy-alpha,alpha-dimethylbenzeneethanimidamide

HRID 1072480Notes

Reaction equation

HRID 1072480 reaction equation
O(C)[Na].Cl.[NH2:5][OH:6].[NH2:7][C:8]1[CH:13]=[C:12]([Cl:14])[C:11]([C:15]([CH3:19])([CH3:18])[C:16]#[N:17])=[C:10]([Cl:20])[CH:9]=1>CO>[NH2:7][C:8]1[CH:9]=[C:10]([Cl:20])[C:11]([C:15]([CH3:18])([CH3:19])[C:16](=[N:5][OH:6])[NH2:17])=[C:12]([Cl:14])[CH:13]=1

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 112416692-(4-Amino-2,6-dichloro-phenyl)-2-methyl-propionitrileHCID 178418582HCID 178418582, compound

Product 1

HCID 544226434-amino-2,6-dichloro-N'-hydroxy-alpha,alpha-dimethylbenzeneethanimidamideYield 26%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

NaOCH3 30% (0.592 mole) was added to a solution of hydroxylamine hydrochloride (0.1085 mole) in CH3OH (200 ml), stirred at RT. The mixture was stirred for 10 minutes. Intermediate (3) (0.0542 mole) was added portionwise and the resulting reaction mixture was stirred and refluxed overnight. The solvent was evaporated. The residue was partitioned between CH2Cl2 and water. The organic layer was separated, dried, filtered and the solvent was evaporated. The residue was stirred in DIPE, filtered off, washed with DIPE, and dried, yielding 3.7 g (26%) of 4-amino-2,6-dichloro-N′-hydroxy-α,α-dimethylbenzeneethanimidamide (intermediate 17).

Workup

  1. stirringThe mixture was stirred for 10 minutes
  2. customthe resulting reaction mixture
  3. stirringwas stirred
  4. temperaturerefluxed overnight
  5. customThe solvent was evaporated
  6. customThe residue was partitioned between CH2Cl2 and water
  7. customThe organic layer was separated
  8. customdried
  9. filtrationfiltered
  10. customthe solvent was evaporated
  11. stirringThe residue was stirred in DIPE
  12. filtrationfiltered off
  13. washwashed with DIPE
  14. customdried

Sources & evidence

ORD record
ord-3dec2af875394d3ea42fa5292f0f9541
Source dataset
uspto-grants-2005_06
Patent number
US06911444B2

Reaction notes

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