4-Toluenesulfonyl chloride → HCID 9554926, compound

HRID 1506509Notes

Reaction equation

HRID 1506509 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.CCOC(C)=O>[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 9554926HCID 9554926, compoundYield 60.4%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of (Z)—N-hydroxybenzimidoyl cyanide (Preparation 103A, 8 g, 55.1 mmol) and 4-methylbenzene-1-sulfonyl chloride (10.51 g, 55.1 mmol) in toluene (70 mL) was heated to reflux. After refluxing for 2 h, the reaction was cooled, diluted with EtOAc (100 mL) and washed with water (50 mL) and brine (50 mL). The organic layer was dried over anhydrous sodium sulfate 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 to reflux
  2. temperatureAfter refluxing for 2 h
  3. temperaturethe reaction was cooled
  4. washwashed with water (50 mL) and brine (50 mL)
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-33d3d5d937e345049d5a86b24361a1b1
Source dataset
uspto-grants-2015_12
Patent number
US09216972B2

Reaction notes

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