(3-Trifluoromethylphenyl)urea → HCID 59684872, compound

HRID 421795Notes

Reaction equation

HRID 421795 reaction equation
[CH:1]1([C:5](=[O:10])[CH2:6][C:7](=O)[CH3:8])[CH2:4][CH2:3][CH2:2]1.[F:11][C:12]([F:24])([F:23])[C:13]1[CH:14]=[C:15]([NH:19][C:20]([NH2:22])=[O:21])[CH:16]=[CH:17][CH:18]=1.[C:25]([C:27]1[CH:34]=[CH:33][C:30]([CH:31]=O)=[CH:29][CH:28]=1)#[N:26]>O1CCCC1>[CH:1]1([C:5]([C:6]2[CH:31]([C:30]3[CH:33]=[CH:34][C:27]([C:25]#[N:26])=[CH:28][CH:29]=3)[NH:22][C:20](=[O:21])[N:19]([C:15]3[CH:16]=[CH:17][CH:18]=[C:13]([C:12]([F:23])([F:24])[F:11])[CH:14]=3)[C:7]=2[CH3:8])=[O:10])[CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 25712(3-Trifluoromethylphenyl)ureaHCID 660424-CyanobenzaldehydeHCID 552735631-Cyclobutylbutane-1,3-dione

Product 1

HCID 59684872HCID 59684872, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred suspension of 1-cyclobutylbutane-1,3-dione (69 mg, 0.49 mmol), N-[3-(trifluoromethyl)phenyl]urea (100 mg, 0.49 mmol) and 4-cyanobenzaldehyde (64.2 mg, 0.49 mmol) in tetrahydrofuran (250 ml) is added polyphosphoric acid ethyl ester (300 mg). The reaction mixture is stirred at reflux for 18 hours. After cooling to room temperature, the solvent is removed in vacuo and the crude product is purified by preparative HPLC (RP18 column; eluent: acetonitrile/0.1% aq. formic acid 10:90→90:10).

Workup

  1. temperatureat reflux for 18 hours
  2. customthe solvent is removed in vacuo
  3. customthe crude product is purified by preparative HPLC (RP18 column; eluent: acetonitrile/0.1% aq. formic acid 10:90→90:10)

Sources & evidence

ORD record
ord-915ba0e7758f4b4e93bc700ee8fae9f0
Source dataset
uspto-grants-2012_01
Patent number
US08101615B2

Reaction notes

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