Benzaldehyde, 3-amino- → 1-(2-Fluorophenyl)-3-(3-formylphenyl)urea

HRID 1960062Notes

Reaction equation

HRID 1960062 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6].[F:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[N:17]=[C:18]=[O:19].S([O-])(O)(=O)=O.[K+]>ClCCCl>[F:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[NH:17][C:18]([NH:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:4]([CH:5]=[O:6])[CH:3]=1)=[O:19]

Participants

5

Reactant 3

HCID 74366Benzaldehyde, 3-amino-HCID 855882-Fluorophenyl isocyanateHCID 516920Potassium bisulfate

Product 1

HCID 873628361-(2-Fluorophenyl)-3-(3-formylphenyl)ureaYield 83.7%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

The product was prepared as described in Example 2, starting with 484 mg of 3-amino-benzaldehyde (4 mmol) (polymerized form) and 548 mg of 2-fluorophenyl isocyanate in 4 ml of DCE. After cooling, the mixture is poured into 100 ml of saturated potassium hydrogen sulfate solution and extracted with twice 50 ml of ethyl acetate. The combined organic phases are washed with water, dried over sodium sulfate and evaporated. 864 mg of the expected aldehyde are isolated in the form of a gum, in an LC/MS purity of 77%. A crystallized fraction is obtained after trituration from ethyl ether. 165 mg of solid are isolated ([M+H]+): 259. RT=4.28 min (acetonitrile/water gradient from 5% to 85%—Method B).

Workup

  1. customThe product was prepared
  2. temperatureAfter cooling
  3. extractionextracted with twice 50 ml of ethyl acetate
  4. washThe combined organic phases are washed with water
  5. dry with materialdried over sodium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-3bc2011ca9144f3e9658c9c27e7328d2
Source dataset
uspto-grants-2013_04
Patent number
US08410286B2

Reaction notes

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