Water → 3,5-Dimethyl-4-thiocyanatoaniline

HRID 1635698Notes

Reaction equation

HRID 1635698 reaction equation
[S-:1][C:2]#[N:3].[NH4+].[CH3:5][C:6]1[CH:7]=[C:8]([CH:10]=[C:11]([CH3:13])[CH:12]=1)[NH2:9].O.C(=O)(O)[O-].[Na+]>CN(C)C=O>[NH2:9][C:8]1[CH:10]=[C:11]([CH3:13])[C:12]([S:1][C:2]#[N:3])=[C:6]([CH3:5])[CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 79493,5-DimethylanilineHCID 15666Ammonium thiocyanateHCID 516892Sodium Bicarbonate

Product 1

HCID 150159523,5-Dimethyl-4-thiocyanatoanilineYield 72.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

251.2 g (3.30 mol) of ammonium thiocyanate are rapidly added to a solution, maintained under a nitrogen atmosphere, of 121.2 g (1 mol) of 3,5-dimethylaniline in 1.75 l of anhydrous N,N-dimethylformamide. The temperature rises from 18 to 35° C. One and a half hours later, the temperature of the solution having returned to room temperature, 263.3 g (1.65 mol) of anhydrous cupric sulphate are added rapidly. The reaction medium is left stirring at room temperature for 3 days and is then poured into 8 l of water. The pH is brought to 7.5 by addition of 550 g (6.55 mol) of sodium bicarbonate. The medium is then filtered, the solid part being washed with ethyl acetate and the liquid part being extracted with ethyl acetate. The combined organic liquid phases are washed with 500 ml of water, dried over sodium sulphate and concentrated to dryness under reduced pressure. The pasty residue obtained is crystallized from 500 ml of hexane to give 128.8 g (72%) of 4-amino-2,6-dimethylphenyl thiocyanate which is used in the next step without further purification.

Workup

  1. customrises from 18 to 35° C
  2. customOne and a half hours
  3. customhaving returned to room temperature
  4. waitThe reaction medium is left
  5. filtrationThe medium is then filtered
  6. washthe solid part being washed with ethyl acetate
  7. extractionthe liquid part being extracted with ethyl acetate
  8. washThe combined organic liquid phases are washed with 500 ml of water
  9. dry with materialdried over sodium sulphate
  10. concentrationconcentrated to dryness under reduced pressure
  11. customThe pasty residue obtained
  12. customis crystallized from 500 ml of hexane

Sources & evidence

ORD record
ord-0498f6d57e884d0ba4b077e37828704e
Source dataset
uspto-grants-2003_01
Patent number
US06509499B1

Reaction notes

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