Sodium Dithionite → HCID 12546817, compound

HRID 1856295Notes

Reaction equation

HRID 1856295 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([O:8][CH2:9][CH2:10][CH3:11])[CH:5]=[C:4]([CH3:12])[C:3]=1[N:13]=NC1C=CC=CC=1.S(S([O-])=O)([O-])=O.[Na+].[Na+]>O>[CH3:1][C:2]1[CH:7]=[C:6]([O:8][CH2:9][CH2:10][CH3:11])[CH:5]=[C:4]([CH3:12])[C:3]=1[NH2:13]

Participants

4

Reactant 2

HCID 24489Sodium DithioniteHCID 545213892,6-Dimethyl-4-propoxyazobenzene

Product 1

HCID 12546817HCID 12546817, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The yield of 2,6-dimethyl-4-propoxyazobenzene (20.2 g) from the previous step was dissolved in 95% alcohol (175 ml). Water was added (160 ml) and the mixture was heated to reflux. Sodium hydrosulfite (Na2S2O4) (44.8 g) was added to the boiling solution in small portions. After completion of this addition, reflux was continued for 30-60 min. The alcohol was removed by distillation at reduced pressure. The remaining heterogeneous residue was made alkaline and was extracted with ether. The ether extract was dried (Na2SO4), filtered, and evaporated. The residual oil was fractionated by distillation in vacuo. After a forerun of aniline, the desired product distilled at 101° C. (0.7 mmHg); nD25 =1.5393. The yield of 2,6-dimethyl-4-propoxyaniline was 6.86 g (51%). Calcd. for C11H17NO: C 73.7, H 9.56, O 8.93. Found: C 73.3, H 9.82, O 8.76.

Workup

  1. temperaturethe mixture was heated to reflux
  2. additionAfter completion of this addition
  3. temperaturereflux
  4. customThe alcohol was removed by distillation at reduced pressure
  5. extractionwas extracted with ether
  6. extractionThe ether extract
  7. dry with materialwas dried (Na2SO4)
  8. filtrationfiltered
  9. customevaporated
  10. distillationThe residual oil was fractionated by distillation in vacuo
  11. distillationAfter a forerun of aniline, the desired product distilled at 101° C. (0.7 mmHg)

Sources & evidence

ORD record
ord-ce8c0296f50b4c42a01ad0be6ee397af
Source dataset
uspto-grants-1980_08
Patent number
US04218477

Reaction notes

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