Ethanolamine → 2-(2,6-Dinitroanilino)ethan-1-ol

HRID 1082050Notes

Reaction equation

HRID 1082050 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12].C(O)C.[CH2:17]([CH2:19][NH2:20])[OH:18]>O>[N+:11]([C:3]1[CH:4]=[CH:5][CH:6]=[C:7]([N+:8]([O-:10])=[O:9])[C:2]=1[NH:20][CH2:19][CH2:17][OH:18])([O-:13])=[O:12]

Participants

5

Reactant 3

HCID 700EthanolamineHCID 702EthanolHCID 118141-Chloro-2,6-dinitrobenzene

Product 1

HCID 233620182-(2,6-Dinitroanilino)ethan-1-olYield 89.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

25 g (0.123 mol) of 1-chloro-2,6-dinitrobenzene are placed in a three-necked, round-bottomed flask containing 180 ml of ethanol. The reaction mixture is heated to 70° C., 22.3 g (0.365 mol) of ethanolamine are added dropwise over 15 minutes and the mixture is left stirring at this temperature for 30 minutes. The temperature of the reaction mixture is left to return to room temperature and 1 liter of water is then added. The product crystallizes, is sucked dry, is washed with water and is dried. There are obtained 25 g of product which is used as is in the following stage.

Workup

  1. waitthe mixture is left
  2. waitThe temperature of the reaction mixture is left
  3. customto return to room temperature
  4. customThe product crystallizes
  5. customis sucked dry
  6. washis washed with water
  7. customis dried

Sources & evidence

ORD record
ord-b53dbceafb154c30bb5947cbc44b6eeb
Source dataset
uspto-grants-1996_12
Patent number
US05589476

Reaction notes

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