Hydrochloric Acid → HCID 135795198, compound

HRID 1033266Notes

Reaction equation

HRID 1033266 reaction equation
[CH3:1][CH2:2][O:3][C:4]1[CH:5]=[CH:6][C:7]([NH2:10])=[CH:8][CH:9]=1.Cl.[N:12]([O-])=O.[Na+].[CH2:16]([C:18]1[CH:19]=[C:20]([OH:24])[CH:21]=[CH:22][CH:23]=1)[CH3:17]>O.[OH-].[Na+]>[CH2:2]([O:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]=[N:12][C:23]2[CH:22]=[CH:21][C:20]([OH:24])=[CH:19][C:18]=2[CH2:16][CH3:17])=[CH:6][CH:5]=1)[CH3:1]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 90764-EthoxyanilineHCID 121013-EthylphenolHCID 23668193Sodium Nitrite

Product 1

HCID 135795198HCID 135795198, compoundYield 61%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
3 °C

Procedure

0.8 mol (109.8 g) of p-phenetidine and 2.1 mol (450 ml) of 16% hydrochloric acid were charged to a round bottomed flask. With cooling of the suspension to about 3° C., 59.2 g (0.8 mol) of NaNO2 dissolved in 320 ml of water was added dropwise over 2.5 hr. During this process the temperature was maintained between 1° and 4° C. After completion of the addition, the mixture was stirred for another 3 hr at 0°-3° C., and was allowed to stand overnight in a refrigerator. A solution of 0.8 mol (97.7 g) of 3-ethylphenol in 800 ml of 2N sodium hydroxide cooled to 5° C. was added dropwise to this suspension at 2° C., over a period of 2 hr, under stirring. An orange-yellow suspension resulted. The reaction mixture was allowed to warm up to room temperature, and was stirred an additional 1 hr. The raw product was then separated by suction filtration and was washed with cold, distilled water. The filter cake was boiled with 2 L of 50:50 ethanol/water mixture, followed by filtration. The resulting 2-phase mixture was allowed to cool under stirring. A brown-red solid precipitated, which was separated by suction filtration, followed by neutral washing. After drying, the product was obtained in a yield of 61% of theoretical.

Workup

  1. additionwas added dropwise over 2.5 hr
  2. temperatureDuring this process the temperature was maintained between 1° and 4° C
  3. additionAfter completion of the addition
  4. waitto stand overnight in a refrigerator
  5. additionwas added dropwise to this suspension at 2° C., over a period of 2 hr
  6. stirringunder stirring
  7. customAn orange-yellow suspension resulted
  8. temperatureto warm up to room temperature
  9. stirringwas stirred an additional 1 hr
  10. customThe raw product was then separated by suction filtration
  11. washwas washed with cold,
  12. distillationdistilled water
  13. filtrationfollowed by filtration
  14. temperatureto cool
  15. stirringunder stirring
  16. customA brown-red solid precipitated
  17. customwhich was separated by suction filtration
  18. customAfter drying
  19. customthe product was obtained in a yield of 61% of theoretical

Sources & evidence

ORD record
ord-430a103f540845f4be5f90698afb349f
Source dataset
uspto-grants-1994_05
Patent number
US05310837

Reaction notes

Loading…