Urea → HCID 178429249, compound

HRID 227706Notes

Reaction equation

HRID 227706 reaction equation
[Cl:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([NH:11][C:12](=[O:17])[CH2:13][C:14](=O)[CH3:15])[CH:9]=2)[NH:4][N:3]=1.[NH2:18][C:19]([NH2:21])=[O:20].FC(F)(F)S([O-])(=O)=O.[Yb+3].FC(F)(F)S([O-])(=O)=O.FC(F)(F)S([O-])(=O)=O.[F:47][C:48]1[CH:55]=[CH:54][C:51]([CH:52]=O)=[CH:50][CH:49]=1>C(#N)C.O>[Cl:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([NH:11][C:12]([C:13]3[CH:52]([C:51]4[CH:54]=[CH:55][C:48]([F:47])=[CH:49][CH:50]=4)[NH:18][C:19](=[O:20])[NH:21][C:14]=3[CH3:15])=[O:17])[CH:9]=2)[NH:4][N:3]=1

Participants

7

Reactant 4

HCID 1176UreaHCID 680234-FluorobenzaldehydeHCID 2733225Ytterbium triflateHCID 178468066HCID 178468066, compound

Product 1

HCID 178429249HCID 178429249, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
100 °C

Procedure

The product from Step (c) (0.25 g, 1.0 mmol), urea (90 mg, 1.5 mmol) and Ytterbium trifluoromethanesulfonate (62 mg, 0.1 mmol) were combined in acetonitrile (5 ml) and 4-Fluorobenzaldehyde (0.11 ml, 1.0 mmol) was added to the mixture. The reaction mixture was sealed and heated to 100° C. for 3 hours. The reaction was diluted with water (1 ml) and the solid product was collected by filtration. The solid was washed three times with 1:1 Et2O/CH3CN to afford the title compound, (0.34 g, 85%); MS (ES+) m/e 401 [M+H]+.

Workup

  1. customThe reaction mixture was sealed
  2. filtrationthe solid product was collected by filtration
  3. washThe solid was washed three times with 1:1 Et2O/CH3CN

Sources & evidence

ORD record
ord-3964054ada0c40b69c19e1503c5ca7bc
Source dataset
uspto-grants-2009_07
Patent number
US07560467B2

Reaction notes

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