Triethylamine → N'-hydroxy-4-(p-tolyl)benzamidine

HRID 923578Notes

Reaction equation

HRID 923578 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]#[N:15])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.C(N(CC)CC)C.Cl.[NH2:24][OH:25].C([O-])(O)=O.[Na+]>CN(C=O)C.O.C(Cl)Cl>[OH:25][N:24]=[C:14]([C:11]1[CH:10]=[CH:9][C:8]([C:5]2[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][CH:4]=2)=[CH:13][CH:12]=1)[NH2:15]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 170889(1,1'-Biphenyl)-4-carbonitrile, 4'-methyl-HCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium Bicarbonate

Product 1

HCID 6860451N'-hydroxy-4-(p-tolyl)benzamidineYield 70.9%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirring solution of 4′-methyl-[1,1′-biphenyl]-4-carbonitrile (524 mg, 2.71 mmol) in DMF (10 mL) were added triethylamine (0.98 mL, 6.78 mmol) and hydroxylamine hydrochloride (471 mg, 6.78 mmol). After stirring at room temperature for 20 h, the reaction mixture was poured into NaHCO3 (50 mL), water (20 mL) and DCM (20 mL) then stirred for 20 min. The precipitate was isolated by filtration using water (2×10 mL) to wash the filter cake. The filter cake was then evaporated with toluene (2×5 mL) and dried under vacuum to afford 435 mg (70%) of N′-hydroxy-4′-methyl-[1,1′-biphenyl]-4-carboximidamide INT-40 as a white solid. LCMS-ESI (m/z) calculated for C14H14N2O: 226; found 227 [M+H]+, tR=1.34 min (Method 10).

Workup

  1. stirringthen stirred for 20 min
  2. customThe precipitate was isolated by filtration
  3. washto wash the filter cake
  4. customThe filter cake was then evaporated with toluene (2×5 mL)
  5. customdried under vacuum

Sources & evidence

ORD record
ord-ef4e2b769f044aa39729de83e4475946
Source dataset
uspto-grants-2016_03
Patent number
US09278910B2

Reaction notes

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