Carbon Disulfide → 2,6-Xylyl isothiocyanate

HRID 65476

Reaction equation

HRID 65476 reaction equation
[H-].[Na+].[CH3:3][C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH3:10])[C:5]=1[NH:11][C:12](=O)C.[H][H].C(=S)=[S:18]>O.C1C=CC=CC=1.CC(N(C)C)=O>[CH3:3][C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH3:10])[C:5]=1[N:11]=[C:12]=[S:18]

Participants

8

Reactant 4

HCID 6348Carbon DisulfideHCID 16616N-Acetyl-2,6-xylidineHCID 24758Sodium hydrideHCID 178418361HCID 178418361, compound

Product 1

HCID 879762,6-Xylyl isothiocyanateYield 74.7%

Reagents, catalysts & solvents 3

HCID 241BenzeneSolventHCID 962WaterSolvent2×HCID 31374DimethylacetamideSolvent

Procedure

To a suspension of 2.5 g (0.05 mol) of sodium hydride in a mixture of 40 ml of dry-dimethylacetamide and 40 ml of dry benzene, 0.05 mole of N-(2,6-dimethylphenyl)acetamide was added. After evolution of hydrogen ceased, the mixture was cooled in ice and water, and with stirring 0.075 mole of carbon disulfide was added slowly. The mixture was stirred at room temperature for 20 minutes. The reaction mixture was poured into water and extracted with toluene. The organic layer, dried over sodium sulfate, was evaporated, and distillation of the residue yielded 6.1 g (74%) of 2,6-dimethylphenylisothiocyanate.

Workup

  1. additionin a mixture of 40 ml
  2. additionwas added
  3. temperaturethe mixture was cooled in ice
  4. additionwas added slowly
  5. extractionextracted with toluene
  6. dry with materialThe organic layer, dried over sodium sulfate
  7. customwas evaporated
  8. distillationdistillation of the residue

Sources & evidence

ORD record
ord-82b7b712d0e94545b1bc2ab0815b792f
Source dataset
uspto-grants-1986_09
Patent number
US04614798

Linked notes

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