Acetyl chloride → HCID 15027380, compound

HRID 1195878Notes

Reaction equation

HRID 1195878 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[CH3:5][C:6]1[C:11]([CH3:12])=[CH:10][CH:9]=[CH:8][C:7]=1[NH:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[CH2:20][NH:21][OH:22].C([O-])(=O)C.[Na+]>O1CCOCC1.O>[CH3:5][C:6]1[C:11]([CH3:12])=[CH:10][CH:9]=[CH:8][C:7]=1[NH:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[CH2:20][N:21]([OH:22])[C:1](=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 517045Sodium AcetateHCID 54173222HCID 54173222, compound

Product 1

HCID 15027380HCID 15027380, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

Acetyl chloride (0.53 g, 6.8 mmol) is added dropwise at 0° C. to a solution of 2-[(2,3-dimethylphenyl)amino]-N-hydroxybenzenemethanamine (1.64 g, 6.8 mmol) and sodium acetate (840 mg, 10 mmol) in 2:1 dioxane/water (100 ml). The reaction mixture is stirred at room temperature for 30 minutes. The product is extracted into ethyl acetate. The organic layer is washed with brine, dried over magnesium sulfate and evaporated to a residue which is recrystallized from cyclohexane to give pure N-[[2-[(2,3-dimethylphenyl)amino]phenyl]methyl]-N-hydroxyacetamide (1.02 g, 53%); mp 93°-98° C.

Workup

  1. extractionThe product is extracted into ethyl acetate
  2. washThe organic layer is washed with brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated to a residue which
  5. customis recrystallized from cyclohexane

Sources & evidence

ORD record
ord-b764cd210a364cadaf4c3c91126b834d
Source dataset
uspto-grants-1992_05
Patent number
US05112846

Reaction notes

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