Hydroxylamine → 3,5-Dibromo-N',4-dihydroxybenzimidamide

HRID 222352

Reaction equation

HRID 222352 reaction equation
[NH2:1][OH:2].[Br:3][C:4]1[CH:5]=[C:6]([CH:9]=[C:10]([Br:13])[C:11]=1[OH:12])[C:7]#[N:8]>O.C(O)C>[Br:3][C:4]1[CH:5]=[C:6]([CH:9]=[C:10]([Br:13])[C:11]=1[OH:12])[C:7](=[N:1][OH:2])[NH2:8]

Participants

5

Reactant 2

HCID 787HydroxylamineHCID 15531Bromoxynil

Product 1

HCID 46396913,5-Dibromo-N',4-dihydroxybenzimidamideYield 75%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Hydroxylamine (10 mL of a 50% solution in water) was added in one portion to a stirred suspension of 3,5-dibromo-4-hydroxybenzonitrile (30 g, 110 mmol) in ethanol (100 mL) at room temperature and the mixture was heated to reflux for 3 hours before cooling back down to room temperature. The solid was filtered, washed with cold ethanol and dried to yield the title compound (25.5 g, 75%) as a colourless powder. 1H NMR δ (ppm) (DMSO-d6): 5.92 (2H, br s), 7.87 (2H, s), 9.69 (1H, br s), 10.19 (1H, br s).

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 3 hours
  3. filtrationThe solid was filtered
  4. washwashed with cold ethanol
  5. customdried

Sources & evidence

ORD record
ord-bec8d5129b844b6a9e414e9effc0a8f4
Source dataset
uspto-grants-2012_06
Patent number
US08207205B2

Linked notes

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