4-Toluenesulfonyl chloride → Benzeneacetonitrile, alpha-[[[(4-methylphenyl)sulfonyl]oxy]imino]-

HRID 1948542Notes

Reaction equation

HRID 1948542 reaction equation
[OH:1]/[N:2]=[C:3](\[C:10]#[N:11])/[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH3:12][C:13]1[CH:18]=[CH:17][C:16]([S:19](Cl)(=[O:21])=[O:20])=[CH:15][CH:14]=1>C1(C)C=CC=CC=1.C(OCC)(=O)C>[S:19]([O:1]/[N:2]=[C:3](\[C:10]#[N:11])/[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)([C:16]1[CH:17]=[CH:18][C:13]([CH3:12])=[CH:14][CH:15]=1)(=[O:21])=[O:20]

Participants

5

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 5464219N-Hydroxybenzimidoyl cyanide

Product 1

HCID 9554926Benzeneacetonitrile, alpha-[[[(4-methylphenyl)sulfonyl]oxy]imino]-Yield 60.4%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of (Z)—N-hydroxybenzimidoyl cyanide (8 g, 55.1 mmol) and 4-methylbenzene-1-sulfonyl chloride (10.51 g, 55.1 mmol) in toluene (70 mL) was heated at reflux. After 2 h, the reaction was allowed to cool, diluted with ethyl acetate (100 mL) and washed with water (50 mL) and brine (50 mL). The organic layer was dried over anhydrous Na2SO4 and concentrated to yield (Z)—N-(tosyloxy)benzimidoyl cyanide (10 g, 33.3 mmol, 60.4% yield) as a light yellow solid.

Workup

  1. temperaturewas heated
  2. temperatureat reflux
  3. temperatureto cool
  4. washwashed with water (50 mL) and brine (50 mL)
  5. dry with materialThe organic layer was dried over anhydrous Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-b99201e9fc2145fca380aae3f4c74cc8
Source dataset
uspto-grants-2013_03
Patent number
US08399451B2

Reaction notes

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