Dimethylamine → HCID 13377160, compound

HRID 1194681Notes

Reaction equation

HRID 1194681 reaction equation
[CH3:1][C:2]1[C:6]2[CH:7]=[C:8]([N+:12]([O-:14])=[O:13])[CH:9]=[C:10]([NH2:11])[C:5]=2[S:4][CH:3]=1.[N:15](OS(=O)(=O)O)=O.[CH3:22][NH:23][CH3:24].[OH-].[Na+]>S(=O)(=O)(O)O>[CH3:22][N:23]([CH3:24])[N:15]=[N:11][C:10]1[C:5]2[S:4][CH:3]=[C:2]([CH3:1])[C:6]=2[CH:7]=[C:8]([N+:12]([O-:14])=[O:13])[CH:9]=1

Participants

6

Reactant 4

HCID 674DimethylamineHCID 14798Sodium HydroxideHCID 82157Nitrosylsulfuric acidHCID 13377159HCID 13377159, compound

Product 1

HCID 13377160HCID 13377160, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

0.05 mole of 3-methyl-5-nitro-7-aminobenzothiophene is dissolved in 100 ml of concentrated sulphuric acid, while cooling with ice, and is diazotised at 10° C. by dropwise addition of 0.05 mole of nitrosylsulphuric acid. After 15 minutes, the mixture is poured onto 700 g of ice, 0.06 mole of dimethylamine (40% strength aqueous dimethylamine solution) is added and the mixture is rendered alkaline with 20% strength sodium hydroxide solution. The triazene is then extracted by shaking with methylene chloride and the organic solution is washed with water and dried over Na2SO4. The crystalline residue obtained after filtration and evaporation of the solvent is taken up in a little methylene chloride and chromatographed on Al2O3 (eluting agent: methylene chloride/cyclohexane (1:1)). The product obtained after evaporation of the eluate is recrystallised from isopropanol.

Workup

  1. temperaturewhile cooling with ice
  2. additionis added
  3. extractionThe triazene is then extracted
  4. washthe organic solution is washed with water
  5. dry with materialdried over Na2SO4
  6. customThe crystalline residue obtained
  7. filtrationafter filtration and evaporation of the solvent
  8. customchromatographed on Al2O3 (eluting agent: methylene chloride/cyclohexane (1:1))
  9. customThe product obtained
  10. customafter evaporation of the eluate
  11. customis recrystallised from isopropanol

Sources & evidence

ORD record
ord-396cd9e4acbe483ea8885f4accd8f269
Source dataset
uspto-grants-1989_03
Patent number
US04816461

Reaction notes

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