Acetone → N-[2-hydroxy-1,1-bis(hydroxymethyl)ethyl]-N'-phenylurea

HRID 1614503Notes

Reaction equation

HRID 1614503 reaction equation
[CH2:1]([OH:8])[C:2]([NH2:7])([CH2:5][OH:6])[CH2:3][OH:4].CC(C)=O.[C:13]1([N:19]=[C:20]=[O:21])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>O>[C:13]1([NH:19][C:20]([NH:7][C:2]([CH2:5][OH:6])([CH2:3][OH:4])[CH2:1][OH:8])=[O:21])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 180AcetoneHCID 6503Tris(hydroxymethyl)aminomethaneHCID 7672Phenyl isocyanate

Product 1

HCID 3996502N-[2-hydroxy-1,1-bis(hydroxymethyl)ethyl]-N'-phenylurea

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

66.6 g (0.55 mol) of tris(hydroxymethyl)aminomethane are dissolved in 200 ml of distilled water, and 400 ml of acetone are added. 59.6 g (0.5 mol) of phenyl isocyanate are added dropwise, while stirring, whereupon a heavy white precipitate forms. When the addition has ended, the mixture is stirred for a further 2 hours and the precipitate is filtered off with suction. It is then digested successively with in each case 150 ml of water, acetone and diethyl ether. Finally, the compound (11), which is obtained in virtually analytically pure form, is dried at 75° C.

Workup

  1. additionWhen the addition
  2. stirringthe mixture is stirred for a further 2 hours
  3. filtrationthe precipitate is filtered off with suction

Sources & evidence

ORD record
ord-38edcfd54fa94d1298c15014a4a5e987
Source dataset
uspto-grants-1993_03
Patent number
US05198322

Reaction notes

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