Urea → HCID 57755858, compound

HRID 227713Notes

Reaction equation

HRID 227713 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[N:7][NH:8]2)=[CH:4][C:3]=1[NH:11][C:12](=[O:17])[CH2:13][C:14](=O)[CH3:15].[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>O>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[N:7][NH:8]2)=[CH:4][C:3]=1[NH:11][C:12]([C:13]1[CH:23]([C:22]2[CH:25]=[CH:26][C:19]([F:18])=[CH:20][CH:21]=2)[NH:27][C:28](=[O:29])[NH:30][C:14]=1[CH3:15])=[O:17]

Participants

6

Reactant 4

HCID 1176UreaHCID 680234-FluorobenzaldehydeHCID 2733225Ytterbium triflateHCID 86018696HCID 86018696, compound

Product 1

HCID 57755858HCID 57755858, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The product from Step (b) (0.100 g, 0.398 mmol, 1.00 equiv), 4-fluorobenzaldehyde (0.0430 mL, 0.398 mmol, 1.00 equiv), urea (36 mg, 0.60 mmol, 1.0 equiv), and ytterbium triflate (25 mg, 0.040 mmol, 0.10 equiv) and heated to 80° C. for 5.5 hours. The reaction was cooled to room temperature and water was added. The precipitate was collected by filtration and washed alternately with CH3CN and Et2O, affording 98 mg (62%) of the title compound. MS (ES+) m/e 400 [M+H].

Workup

  1. filtrationThe precipitate was collected by filtration
  2. washwashed alternately with CH3CN and Et2O

Sources & evidence

ORD record
ord-f0fd92a4eeec4533b3993234a6a2966b
Source dataset
uspto-grants-2009_07
Patent number
US07560467B2

Reaction notes

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