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

HRID 982491Notes

Reaction equation

HRID 982491 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-24c87e32ac924085a0ae7e497f9fea1e
Source dataset
uspto-grants-1991_02
Patent number
US04996301

Reaction notes

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