Dimethyl Sulfoxide → Methylbiphenyl-2-carboxamidoxime

HRID 5231

Reaction equation

HRID 5231 reaction equation
Cl.[NH2:2][OH:3].C[O-].[Na+].[Na].[C:8]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[C:16]1[CH:21]=[CH:20][C:19](C)=[CH:18][CH:17]=1)#[N:9].[CH3:23]S(C)=O>CO>[CH3:23][C:15]1[CH:14]=[CH:13][CH:12]=[C:11]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:10]=1[C:8](=[N:2][OH:3])[NH2:9]

Participants

7

Reactant 5

HCID 679Dimethyl SulfoxideHCID 1455122-Cyano-4'-methylbiphenylHCID 443297Hydroxyamine hydrochlorideHCID 5360545SodiumHCID 10942334Sodium Methoxide

Product 1

HCID 131718116Methylbiphenyl-2-carboxamidoxime

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of hydroxylamine hydrochloride (17.9 g) in dimethyl sulfoxide (120 ml) was added a methanol solution of sodium methoxide prepared from metallic sodium (5.92 g) and anhydrous methanol (50 ml). The mixture was stirred for 10 minutes at room temperature, to which was added 2'-cyano-4-methylbiphenyl (10 g) The reaction mixture was stirred for 5 hours at 100° C. The reaction mixture was partitioned between ethyl acetate and water. The aqueous layer was extracted with ethyl acetate. Organic layers were combined, washed with water and dried, then the solvent was evaporated in vacuo. The residue was purified by column chromatography on silica gel to afford the title compound as a white amorphous product (11.2 g, 96%).

Workup

  1. stirringwas stirred for 5 hours at 100° C
  2. customThe reaction mixture was partitioned between ethyl acetate and water
  3. extractionThe aqueous layer was extracted with ethyl acetate
  4. washwashed with water
  5. customdried
  6. customthe solvent was evaporated in vacuo
  7. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-b2e4e352ee244261996ff42a33ea5c0d
Source dataset
uspto-grants-1993_09
Patent number
US05243054

Linked notes

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