Toluene → HCID 86679350, compound

HRID 1498938Notes

Reaction equation

HRID 1498938 reaction equation
C1(C)C=CC=CC=1.[Cl:8][C:9]1[CH:14]=[C:13]([Cl:15])[CH:12]=[CH:11][C:10]=1[C:16](=[N:19][OH:20])[C:17]#[N:18].[S:21](Cl)([C:24]1[CH:30]=[CH:29][C:27]([CH3:28])=[CH:26][CH:25]=1)(=[O:23])=[O:22]>C(N(CC)CC)C>[Cl:8][C:9]1[CH:14]=[C:13]([Cl:15])[CH:12]=[CH:11][C:10]=1[C:16](=[N:19][O:20][S:21]([C:24]1[CH:30]=[CH:29][C:27]([CH3:28])=[CH:26][CH:25]=1)(=[O:23])=[O:22])[C:17]#[N:18]

Participants

5

Reactant 3

HCID 1140TolueneHCID 73974-Toluenesulfonyl chlorideHCID 2743095HCID 2743095, compound

Product 1

HCID 86679350HCID 86679350, compoundYield 77.2%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To toluene (200 ml), (2,4-dichlorophenyl)-hydroxyiminoacetonitrile (8.60 g, 40 mmol) prepared in the Step 27-1-1, tosyl chloride (9.50 g) and triethylamine (5.0 g) were added, and the mixture was heated under reflux for 5 hours. After being allowed to cool, the mixture was washed with water and dried over anhydrous magnesium sulfate. The resulting residue was purified by silica gel column chromatography (ethyl acetate:n-hexane=1:3) to give the title compound (11.4 g, 77%).

Workup

  1. additionwere added
  2. temperaturethe mixture was heated
  3. temperatureunder reflux for 5 hours
  4. temperatureto cool
  5. washthe mixture was washed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe resulting residue was purified by silica gel column chromatography (ethyl acetate:n-hexane=1:3)

Sources & evidence

ORD record
ord-95f04e2f845c4592b6e949d33481148c
Source dataset
uspto-grants-2015_12
Patent number
US09200008B2

Reaction notes

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