Dimethyl Sulfoxide → N-Hydroxy-4-iodo-benzamidine

HRID 1045376Notes

Reaction equation

HRID 1045376 reaction equation
Cl.[NH2:2][OH:3].C(N(CC)CC)C.CS(C)=O.[I:15][C:16]1[CH:23]=[CH:22][C:19]([C:20]#[N:21])=[CH:18][CH:17]=1>C1COCC1.O>[OH:3][N:2]=[C:20]([C:19]1[CH:22]=[CH:23][C:16]([I:15])=[CH:17][CH:18]=1)[NH2:21]

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 764674-IodobenzonitrileHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 4429393N-Hydroxy-4-iodo-benzamidine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

17.3 g (249 mmol) of hydroxylamine hydrochloride and then 35 ml (251 mmol) of triethylamine are added to 80 ml of DMSO. A voluminous white precipitate forms, and the reaction mixture is diluted with a small amount of THF. After stirring for 1 hour, the precipitate is filtered off. The filtrate is collected and then transferred to a flask to which there are added 9.55 g (41.7 mmol) of 4-iodobenzonitrile. The reaction mixture is stirred overnight at ambient temperature and is then cooled in an ice bath and 200 mL of water are added. The precipitate is filtered off to yield the expected product.

Workup

  1. filtrationthe precipitate is filtered off
  2. customThe filtrate is collected
  3. customtransferred to a flask to which there
  4. stirringThe reaction mixture is stirred overnight at ambient temperature
  5. temperatureis then cooled in an ice bath
  6. filtrationThe precipitate is filtered off

Sources & evidence

ORD record
ord-1cf290905e394da4b13bfdb9f3143a27
Source dataset
uspto-grants-2013_10
Patent number
US08569285B2

Reaction notes

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