N-Phenyl diethanolamine → Ethanol, 2,2'-((4-nitrosophenyl)imino)bis-

HRID 918209Notes

Reaction equation

HRID 918209 reaction equation
[C:1]1([N:7]([CH2:11][CH2:12][OH:13])[CH2:8][CH2:9][OH:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N:14]([O-])=[O:15].[Na+]>Cl.O>[N:14]([C:4]1[CH:5]=[CH:6][C:1]([N:7]([CH2:11][CH2:12][OH:13])[CH2:8][CH2:9][OH:10])=[CH:2][CH:3]=1)=[O:15]

Participants

5

Reactant 2

HCID 8416N-Phenyl diethanolamineHCID 23668193Sodium Nitrite

Product 1

HCID 77143Ethanol, 2,2'-((4-nitrosophenyl)imino)bis-

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

23.9 g of N-phenyldiethanol amine were ground in a mortar and dissolved in 50 ml conc. HCl. The solution was then cooled to 0°C and 10 g NaNO2 in 25 ml of water were added over a period of one hour with stirring. The temperature was maintained between 0°-5°C. After the addition was complete, the mixture was stirred one hour more and then filtered. The orange precipitate of 4-nitroso-N,N-bis-(β-hydroxyethyl) aniline formed was dried in a vacuum desiccator overnight. The dried product, amounting to 25.0 g was suspended in 150 ml. isopropanol and reduced on a Parr hydrogenator over Pt/C. When the loss in pressure approached theoretical, the mixture was filtered into a flask containing 200 ml. isopropanol saturated with HCl gas. A stream of HCl gas was passed through the filtrate during the filtration and for about 20 minutes after the filtration was complete. The white precipitate of N,N-bis-(β-hydroxyethyl)-p-phenylenediamine hydrochloride was collected and weighed. Yield 19.8 g.

Workup

  1. temperatureThe temperature was maintained between 0°-5°C
  2. additionAfter the addition
  3. stirringthe mixture was stirred one hour more
  4. filtrationfiltered

Sources & evidence

ORD record
ord-727eb30664594b729736e9a6f9404d2c
Source dataset
uspto-grants-1976_07
Patent number
US03970423

Reaction notes

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