Sodium Hydroxide → HCID 178424052, compound

HRID 2248443Notes

Reaction equation

HRID 2248443 reaction equation
[N+:1]([C:4]1[C:10]([CH3:11])=[C:9]([CH3:12])[CH:8]=[C:7]([CH3:13])[C:5]=1[NH2:6])([O-])=O.C(O[C:17]([S-])=[S:18])C.[K+].[OH-].[Na+]>C(O)C.[Pd].[H][H].O>[CH3:11][C:10]1[C:4]2[N:1]=[C:17]([SH:18])[NH:6][C:5]=2[C:7]([CH3:13])=[CH:8][C:9]=1[CH3:12]

Participants

8

Reactant 3

HCID 14798Sodium HydroxideHCID 2735045Potassium ethylxanthateHCID 19996504HCID 19996504, compound

Product 1

HCID 178424052HCID 178424052, compoundYield 66%

Reagents, catalysts & solvents 4

HCID 702EthanolSolventHCID 962WaterSolventHCID 23938PalladiumSolventHCID 178418361HCID 178418361, compoundSolvent

Procedure

2-Nitro-3,4,6-trimethylaniline (10.2 g, 0.057 mol) was dissolved in 95% ethanol (900 ml) and hydrogenated in the presence of Pd/C-catalyst until the theoretical amount of hydrogen had been consumed (1 hour). The whole mixture was transferred to another flask and potassium ethylxanthate (12.8 g, 0.080 mol) dissolved in water (12.5 ml) was added. The mixture was refluxed overnight, 2M NaOH (20 ml) was added and the volatiles were evaporated off. The residue was dissolved in methanol (300 ml) and the catalyst was filtered off. Part of the solvent (200 ml) was evaporated off. Water (100 ml) was added and the mixture was acidified with acetic acid (10 ml) dissolved in water (20 ml). The crystalline precipitate was filtered off, washed with water and dried under reduced pressure, giving the desired product (7.2 g, 66%), NMR: δ (CDCl3) 2.0(s,3H), 2.05(s,3H), 2.1(s,3H), 3.3(br.s, 1H), 6.5(s,1H).

Workup

  1. customhad been consumed (1 hour)
  2. customThe whole mixture was transferred to another flask
  3. additionwas added
  4. temperatureThe mixture was refluxed overnight
  5. customthe volatiles were evaporated off
  6. dissolutionThe residue was dissolved in methanol (300 ml)
  7. filtrationthe catalyst was filtered off
  8. customPart of the solvent (200 ml) was evaporated off
  9. additionWater (100 ml) was added
  10. dissolutiondissolved in water (20 ml)
  11. filtrationThe crystalline precipitate was filtered off
  12. washwashed with water
  13. customdried under reduced pressure

Sources & evidence

ORD record
ord-553f19211fad4a49bf1c76849005be46
Source dataset
uspto-grants-1991_08
Patent number
US05039806

Reaction notes

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