(3-Trifluoromethylphenyl)urea → HCID 59218311, compound

HRID 1366247Notes

Reaction equation

HRID 1366247 reaction equation
[CH:1]([C:3]1[CH:4]=[CH:5][C:6]([C:9]#[N:10])=[N:7][CH:8]=1)=O.[CH3:11][C:12](=O)[CH2:13][C:14](=[O:16])[CH3:15].[F:18][C:19]([F:31])([F:30])[C:20]1[CH:21]=[C:22]([NH:26][C:27]([NH2:29])=[O:28])[CH:23]=[CH:24][CH:25]=1>O1CCCC1.CS(C)=O>[C:14]([C:13]1[CH:1]([C:3]2[CH:4]=[CH:5][C:6]([C:9]#[N:10])=[N:7][CH:8]=2)[NH:29][C:27](=[O:28])[N:26]([C:22]2[CH:23]=[CH:24][CH:25]=[C:20]([C:19]([F:30])([F:31])[F:18])[CH:21]=2)[C:12]=1[CH3:11])(=[O:16])[CH3:15]

Participants

6

Reactant 3

HCID 25712(3-Trifluoromethylphenyl)ureaHCID 31261AcetylacetoneHCID 109862635-Formylpyridine-2-carbonitrile

Product 1

HCID 59218311HCID 59218311, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of Example 3A (75 mg, 0.57 mmol) in tetrahydrofuran (5 ml) is given 2,4-pentandione (57 mg, 0.57 mmol), N-[3-(trifluoromethyl)phenyl]urea (116 mg, 0.57 mmol) and polyphosphoric acid ethyl ester (200 mg) [freshly prepared according to the procedure of Cava et al., J. Org. Chem. 34, 2665 (1969)]. The reaction mixture is refluxed for 24 hours after which time the solution is diluted with DMSO (2 ml) and purified by preparative HPLC.

Workup

  1. customfreshly prepared
  2. temperatureThe reaction mixture is refluxed for 24 hours after which time the solution
  3. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-a57ad6bae79e4ab48f25d64888e43cf2
Source dataset
uspto-grants-2011_02
Patent number
US07893073B2

Reaction notes

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