Urea → HCID 57755848, compound

HRID 227719Notes

Reaction equation

HRID 227719 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:11][C:12](=[O:17])[CH2:13][C:14](=O)[CH3:15])[CH:5]=[C:6]2[C:10]=1[NH:9][N:8]=[CH:7]2.[CH:18]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:21]=[CH:20][C:19]=1[CH:28]=O.[NH2:30][C:31]([NH2:33])=[O:32].[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:3]=[C:4]([NH:11][C:12]([C:13]2[CH:28]([C:19]3[CH:20]=[CH:21][C:22]4[C:27](=[CH:26][CH:25]=[CH:24][CH:23]=4)[CH:18]=3)[NH:30][C:31](=[O:32])[NH:33][C:14]=2[CH3:15])=[O:17])[CH:5]=[C:6]2[C:10]=1[NH:9][N:8]=[CH:7]2

Participants

6

Reactant 4

HCID 1176UreaHCID 62012-NaphthalenecarboxaldehydeHCID 2733225Ytterbium triflateHCID 86018698HCID 86018698, compound

Product 1

HCID 57755848HCID 57755848, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The product from Example 139, Step (b) (87.3 mg, 0.348 mmol, 1.00 equiv), 2-naphthaldehyde (54 mg, 0.348 mmol, 1.00 equiv), urea (32 mg, 0.53 mmol, 1.0 equiv), and ytterbium triflate (22 mg, 0.035 mmol, 0.10 equiv) and heated to 80° C. for 2 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 78 mg (52%) of the title compound. MS (ES+) m/e 432 [M+H].

Workup

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

Sources & evidence

ORD record
ord-49f9d494c6e04cba8a73f61f181e1511
Source dataset
uspto-grants-2009_07
Patent number
US07560467B2

Reaction notes

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