Ethanolamine → HCID 21249788, compound

HRID 1531627Notes

Reaction equation

HRID 1531627 reaction equation
[NH2:1][CH2:2][CH2:3][OH:4].C(#N)C.[N+:8]([C:11]1[CH:12]=[C:13]([N:20]=[C:21]=[O:22])[CH:14]=[C:15]([N+:17]([O-:19])=[O:18])[CH:16]=1)([O-:10])=[O:9]>O>[N+:8]([C:11]1[CH:12]=[C:13]([NH:20][C:21]([NH:1][CH2:2][CH2:3][OH:4])=[O:22])[CH:14]=[C:15]([N+:17]([O-:19])=[O:18])[CH:16]=1)([O-:10])=[O:9]

Participants

5

Reactant 3

HCID 700EthanolamineHCID 6342Acetonitrile2×HCID 1940873,5-Dinitrophenyl isocyanate2×

Product 1

HCID 21249788HCID 21249788, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

11.0 g (0.180 mol) of 2-aminoethanol was placed, in a nitrogen current, in a 0.3-l four-necked flask equipped with a nitrogen inlet tube, a dropping funnel, a reflux condenser, a thermometer and a mixing blade. Thereto was added 50 ml of acetonitrile, followed by stirring for dissolution. While the flask was being cooled with ice water, the flask contents were stirred. Thereto was dropwise added 50 ml of the above-obtained acetonitrile solution containing 3,5-dinitrophenyl isocyanate (compound 7). The mixture was stirred at room temperature for 1 hour and then poured into 0.7 l of water. The separated crystals were collected by suction filtration, washed with water and vacuum-dried at 35° C. for 12 hours to obtain N-(3,5-dinitrophenyl)-N′-(2-hydroxyethyl)urea (compound 11) as a yellow powder. Yield: 16.7 g (74%) Melting point: 192-194° C.

Workup

  1. customequipped with a nitrogen inlet tube, a dropping funnel, a reflux condenser
  2. stirringthe flask contents were stirred
  3. stirringThe mixture was stirred at room temperature for 1 hour
  4. filtrationThe separated crystals were collected by suction filtration
  5. washwashed with water
  6. customvacuum-dried at 35° C. for 12 hours

Sources & evidence

ORD record
ord-d51a4ee3118d4e3e8b446a261d1cf9a7
Source dataset
uspto-grants-2001_03
Patent number
US06200831B1

Reaction notes

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