2,4-Dimethylaniline → HCID 131711588, compound

HRID 972077Notes

Reaction equation

HRID 972077 reaction equation
[CH3:1][C:2]1[CH:8]=[C:7]([CH3:9])[CH:6]=[CH:5][C:3]=1[NH2:4].C(N(CC)CC)C.[Cl-].[Cl:18][C:19]1[S:20][S+:21]=[C:22](Cl)[C:23]=1[Cl:24]>C(Cl)Cl>[Cl:24][C:23]1[C:22](=[N:4][C:3]2[CH:5]=[CH:6][C:7]([CH3:9])=[CH:8][C:2]=2[CH3:1])[S:21][S:20][C:19]=1[Cl:18]

Participants

5

Reactant 3

HCID 72502,4-DimethylanilineHCID 8471TriethylamineHCID 11379498HCID 11379498, compound

Product 1

HCID 131711588HCID 131711588, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
20 °C

Procedure

14.0 g of 2,4-dimethyl-aniline were dissolved in 300 ml of methylene chloride and 50 ml of triethylamine and 31.0 g of 3,4,5-trichloro-1,2-dithiolium chloride were introduced at 10°-15° C. After stirring for three hours at 20° C., a test for aromatic amine, by diazotizing and coupling, proved negative. The resulting dark solution was then washed three times with 200 ml of water, dried over potassium carbonate and filtered over a column of aluminum oxide, to remove impurities that imparted a color. The filtrate was concentrated and caused to crystallize by adding petroleum ether. Yield, 17.0 g of yellowish crystals; melting point: 72°-74° C. The elementary analysis and NMR spectrum agreed with the assumed structure.

Workup

  1. washThe resulting dark solution was then washed three times with 200 ml of water
  2. dry with materialdried over potassium carbonate
  3. filtrationfiltered over a column of aluminum oxide
  4. customto remove impurities that
  5. concentrationThe filtrate was concentrated
  6. customto crystallize
  7. additionby adding petroleum ether
  8. customYield

Sources & evidence

ORD record
ord-b17d7201c432463bb0b24dfff14a78a0
Source dataset
uspto-grants-1979_07
Patent number
US04163059

Reaction notes

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