Sodium Hydroxide → HCID 22408500, compound

HRID 439872Notes

Reaction equation

HRID 439872 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:6]=[C:7]([CH3:12])[C:8]=1[O:9][CH2:10][CH3:11])[NH2:5].[N:13]([O-])=O.[Na+].S(S([O-])=O)([O-])=O.[Na+].[Na+].[OH-].[Na+]>Cl.O.CCOCC>[CH3:1][C:2]1[CH:3]=[C:4]([NH:5][NH2:13])[CH:6]=[C:7]([CH3:12])[C:8]=1[O:9][CH2:10][CH3:11]

Participants

8

Reactant 4

HCID 14798Sodium HydroxideHCID 24489Sodium DithioniteHCID 133357494-Ethoxy-3,5-dimethylanilineHCID 23668193Sodium Nitrite

Product 1

HCID 22408500HCID 22408500, compoundYield 93.6%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent2×HCID 3283Diethyl EtherSolvent

Procedure

To a cooled (+5° C.), stirred suspension of 9.2 g (0.0557 mol) of 3,5-dimethyl-4-ethoxyaniline in 50 ml of 6N HCl (aq), 3.8 g (0.0557 mol) of NaNO2 in 15 ml of water was added during 30 minutes. After stirring at +5° C. for 30 minutes further, the resulting mixture was added under argon and stirring to 29.1 g (0.167 mol) of sodium dithionite dissolved in 150 ml of water. After stirring for 20 minutes at +5° C., 250 ml of ether was added followed by alkalinization to pH 9 with 10N sodium hydroxide solution. The organic phase was separated and washed with sodium chloride solution. After drying (Na2SO4) the product was precipitated as the hydrochloride by addition of HCl(g)/ether (to pH 3). Filtration and washing with ether gave 9.4 g (78%) of the product.

Workup

  1. temperatureTo a cooled (+5° C.)
  2. additionwas added during 30 minutes
  3. stirringAfter stirring at +5° C. for 30 minutes further
  4. additionthe resulting mixture was added under argon
  5. stirringAfter stirring for 20 minutes at +5° C.
  6. customThe organic phase was separated
  7. washwashed with sodium chloride solution
  8. dry with materialAfter drying (Na2SO4) the product
  9. customwas precipitated as the hydrochloride by addition of HCl(g)/ether (to pH 3)
  10. filtrationFiltration
  11. washwashing with ether

Sources & evidence

ORD record
ord-d010e1eaf73c4e5a93bb6d36bc9082dd
Source dataset
uspto-grants-1996_05
Patent number
US05516788

Reaction notes

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