Urea → HCID 57755927, compound

HRID 227711Notes

Reaction equation

HRID 227711 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([NH:10][C:11](=[O:17])[CH2:12][C:13](=O)[CH2:14][CH3:15])=[CH:7][CH:8]=2)[CH:3]=[N:2]1.[F:18][C:19]1[CH:26]=[CH:25][C:22]([CH:23]=O)=[CH:21][CH:20]=1.[NH2:27][C:28]([NH2:30])=[O:29].[O-]S(C(F)(F)F)(=O)=O.[Yb+3].[O-]S(C(F)(F)F)(=O)=O.[O-]S(C(F)(F)F)(=O)=O>CC#N.O>[CH2:14]([C:13]1[NH:30][C:28](=[O:29])[NH:27][CH:23]([C:22]2[CH:25]=[CH:26][C:19]([F:18])=[CH:20][CH:21]=2)[C:12]=1[C:11]([NH:10][C:6]1[CH:5]=[C:4]2[C:9](=[CH:8][CH:7]=1)[NH:1][N:2]=[CH:3]2)=[O:17])[CH3:15]

Participants

7

Reactant 4

HCID 1176UreaHCID 680234-FluorobenzaldehydeHCID 2733225Ytterbium triflateHCID 86018694HCID 86018694, compound

Product 1

HCID 57755927HCID 57755927, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

The product of Step (a) (126 mg, 0.545 mmol, 1 equiv), 4-fluorobenzaldehyde (0.058 mL, 0.545 mmol, 1 equiv), urea (49 mg, 0.818 mmol, 1.5 equiv), and ytterbium triflate (37 mg, 0.06 mol, 0.10 equiv) were combined in CH3CN (2 mL) and heated to reflux for 4.5 hours. The reaction was diluted with water and the resulting precipitate was collected by filtration. The solid was washed with water, CH3CN, and Et2O. 140 mg (68%) of the product was isolated as a pale grey solid. MS (ES+) m/e 380 [M+H]+.

Workup

  1. temperatureheated
  2. temperatureto reflux for 4.5 hours
  3. filtrationthe resulting precipitate was collected by filtration
  4. washThe solid was washed with water, CH3CN, and Et2O

Sources & evidence

ORD record
ord-0ca5ddafbc5f465a9506d4efafef601c
Source dataset
uspto-grants-2009_07
Patent number
US07560467B2

Reaction notes

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