Dimethyl Sulfoxide → 4,N-Dihydroxy-benzamidine

HRID 644129Notes

Reaction equation

HRID 644129 reaction equation
CS(C)=O.[C:5]([C:7]1[CH:12]=[CH:11][C:10](O)=[CH:9][CH:8]=1)#[N:6].[NH2:14][OH:15].[OH-:16].[Na+]>O.C(Cl)(Cl)Cl>[OH:15][N:14]=[C:5]([NH2:6])[C:7]1[CH:12]=[CH:11][C:10]([OH:16])=[CH:9][CH:8]=1

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 787HydroxylamineHCID 130194-CyanophenolHCID 14798Sodium Hydroxide

Product 1

HCID 51497564,N-Dihydroxy-benzamidine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

To a dimethylsulfoxide (100 mL) solution of 10.0 g of 4-cyanophenol was dropwise added 12.9 mL of a 50% hydroxylamine aqueous solution at room temperature over a period of 6 minutes, which was then stirred at the same temperature for 14 hours. Chloroform, a 1 mol/L sodium hydroxide aqueous solution, and water were added to the reaction mixture. The aqueous layer was separated and washed sequentially with toluene, chloroform, and toluene, to which water was then added, followed by adjustment to pH 7.2 using 6 mol/L hydrochloric acid. After stirring this mixture at room temperature for 30 minutes, the precipitate was collected by filtration and washed with water to provide 8.88 g of N′, 4-dihydroxybenzamidine as white solid form.

Workup

  1. customat room temperature
  2. customof 6 minutes
  3. customThe aqueous layer was separated
  4. washwashed sequentially with toluene, chloroform, and toluene, to which water
  5. additionwas then added
  6. stirringAfter stirring this mixture at room temperature for 30 minutes
  7. filtrationthe precipitate was collected by filtration
  8. washwashed with water

Sources & evidence

ORD record
ord-cdc973003f8e4cbd9cd7b8188a94286c
Source dataset
uspto-grants-2010_04
Patent number
US07700623B2

Reaction notes

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