Hydrochloric Acid → 2-(N-ethyl-p-nitrosoanilino)ethanol

HRID 653140Notes

Reaction equation

HRID 653140 reaction equation
[N:1]([O-:3])=O.[Na+].[CH2:5]([N:7]([CH2:14][CH2:15][OH:16])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH3:6].Cl.[OH-].[Na+]>O.C1C=CC=CC=1>[CH2:5]([N:7]([CH2:14][CH2:15][OH:16])[C:8]1[CH:9]=[CH:10][C:11]([N:1]=[O:3])=[CH:12][CH:13]=1)[CH3:6]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 623382-(N-ethylanilino)ethanolHCID 23668193Sodium Nitrite

Product 1

HCID 672812-(N-ethyl-p-nitrosoanilino)ethanolYield 59.6%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 962WaterSolvent2×

Procedure

A solution was prepared by dissolving 18.5 g (0.26 mol) of sodium nitrite, of a purity of 97%, in 30 ml of water. This solution was added dropwise to a solution composed of 41.3 g (0.25 mol) of N-ethyl-N-2-hydroxyethylaniline, 200 g of water and 105 ml of conc HCl with stirring at a temperature between 5° and 10° C. for one-half hour. After stirring the solution obtained at a temperature between 10° and 20° C. for one hour, the solution was neutralized to pH 8 with a 15% aqueous solution of sodium hydroxide. 100 ml of benzene was added to the neutralized solution with stirring. After standing, the organic phase of the solution was separated. The benzene of the organic phase obtained was removed under reduced pressure. 28.9 g of N-ethyl-N-2-hydroxyethyl-p-nitrosoaniline which is a dark brown colored viscous liquid was obtained. The yield was 59.6%.

Workup

  1. customA solution was prepared
  2. additionThis solution was added dropwise to a solution
  3. stirringAfter stirring the solution
  4. customobtained at a temperature between 10° and 20° C. for one hour
  5. stirringwith stirring
  6. customthe organic phase of the solution was separated
  7. customThe benzene of the organic phase obtained
  8. customwas removed under reduced pressure
  9. customwas obtained

Sources & evidence

ORD record
ord-bbcbd0a4a5c243e5b5ed6cb42b5d1f2e
Source dataset
uspto-grants-1987_06
Patent number
US04675355

Reaction notes

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