Phenyl isocyanate → 1-(2-dimethylaminoethyl)-3-phenylurea

HRID 223275Notes

Reaction equation

HRID 223275 reaction equation
[CH3:1][N:2]([CH2:4][CH2:5][NH2:6])[CH3:3].[C:7]1([N:13]=[C:14]=[O:15])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>C1(C)C=CC=CC=1>[C:7]1([NH:13][C:14]([NH:6][CH2:5][CH2:4][N:2]([CH3:3])[CH3:1])=[O:15])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 7672Phenyl isocyanateHCID 66053N,N-Dimethylethylenediamine

Product 1

HCID 15265811-(2-dimethylaminoethyl)-3-phenylurea

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

88 g of dimethylaminoethylamine are dissolved in 500 l of toluene and then 119 g of phenyl isocyanate are added dropwise in the course of 10 minutes, whereupon the temperature rises to 97° C. The mixture is refluxed for 4 hours. On cooling, the product crystallises and is filtered with suction. The moist product is recrystallised from 1000 ml of ethyl acetate. Yield: 135 g (65.1%); m.p. 141°-142° C.

Workup

  1. customrises to 97° C
  2. temperatureThe mixture is refluxed for 4 hours
  3. temperatureOn cooling
  4. customthe product crystallises
  5. filtrationis filtered with suction
  6. customThe moist product is recrystallised from 1000 ml of ethyl acetate

Sources & evidence

ORD record
ord-c2154438549241f3a25316de9488dbb0
Source dataset
uspto-grants-1982_10
Patent number
US04352913

Reaction notes

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