Acetamide → 2,6-Xylyl isothiocyanate

HRID 65474

Reaction equation

HRID 65474 reaction equation
[C:1]([NH2:4])(=O)[CH3:2].[H-].[Na+].[H][H].[C:9](=[S:11])=S.[CH3:12]N(C)C(=O)C.[CH:18]1[CH:23]=[CH:22]C=[CH:20][CH:19]=1>CN(C)C(=O)C.C1(C)C=CC=CC=1.O1CCCC1>[CH3:12][C:2]1[CH:20]=[CH:19][CH:18]=[C:23]([CH3:22])[C:1]=1[N:4]=[C:9]=[S:11]

Participants

8

Reactant 5

HCID 178AcetamideHCID 6348Carbon DisulfideHCID 24758Sodium hydrideHCID 21705219N,N-Dimethylacetamide--benzene (1/1)HCID 178418361HCID 178418361, compound

Product 1

HCID 879762,6-Xylyl isothiocyanate

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 66603805toluene N,N-dimethylacetamideSolvent

Procedure

Briefly, this preparation involves first adding the acetamide to a suspension of sodium hydride in an organic solvent, preferably a N,N-dimethylacetamide/benzene solvent system. The cessation of hydrogen indicates completion of the reaction after which the reaction mixture is cooled and carbon disulfide added slowly. When tetrahydrofuran is the solvent employed, a reaction time of approximately 1.5 hours is required to provide yields in excess of 80 percent while when a mixture of N,N-dimethylacetamide/toluene is used, yields in excess of 80 percent are obtained in approximately 20 minutes.

Workup

  1. customcompletion of the reaction after which the reaction mixture
  2. temperatureis cooled
  3. customa reaction time of approximately 1.5 hours
  4. customto provide
  5. customyields in excess of 80 percent while when
  6. customyields in excess of 80 percent
  7. customare obtained in approximately 20 minutes

Sources & evidence

ORD record
ord-69321b9344924861a5eab92e23c20ff5
Source dataset
uspto-grants-1986_09
Patent number
US04614798

Linked notes

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