(3-Trifluoromethylphenyl)urea → HCID 59411352, compound

HRID 1366248Notes

Reaction equation

HRID 1366248 reaction equation
[CH:1]([C:3]1[CH:4]=[CH:5][C:6]([C:9]#[N:10])=[N:7][CH:8]=1)=O.O=[C:12]([CH3:20])[CH2:13][C:14]([O:16][CH2:17][CH:18]=[CH2:19])=[O:15].[F:21][C:22]([F:34])([F:33])[C:23]1[CH:24]=[C:25]([NH:29][C:30]([NH2:32])=[O:31])[CH:26]=[CH:27][CH:28]=1>O1CCCC1>[C:9]([C:6]1[N:7]=[CH:8][C:3]([CH:1]2[C:13]([C:14]([O:16][CH2:17][CH:18]=[CH2:19])=[O:15])=[C:12]([CH3:20])[N:29]([C:25]3[CH:26]=[CH:27][CH:28]=[C:23]([C:22]([F:33])([F:34])[F:21])[CH:24]=3)[C:30](=[O:31])[NH:32]2)=[CH:4][CH:5]=1)#[N:10]

Participants

5

Reactant 3

HCID 25712(3-Trifluoromethylphenyl)ureaHCID 70701Allyl acetoacetateHCID 109862635-Formylpyridine-2-carbonitrile

Product 1

HCID 59411352HCID 59411352, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of Example 3A (29.3 g, 70.4 mmol) in tetrahydrofuran (450 ml) is given allyl 3-oxobutanoate (10.0 g, 70.4 mmol), N-[3-(trifluoromethyl)phenyl]urea (14.4 g, 70.4 mmol) and polyphosphoric acid ethyl ester (33 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 solvent is removed in vacuo, and the residue is purified by column chromatography (silica, eluent: cyclohexane/ethyl acetate mixtures).

Workup

  1. customfreshly prepared
  2. temperatureThe reaction mixture is refluxed for 24 hours after which time the solvent
  3. customis removed in vacuo
  4. customthe residue is purified by column chromatography (silica, eluent: cyclohexane/ethyl acetate mixtures)

Sources & evidence

ORD record
ord-b34850007cec47a68afae3fe9281d5d0
Source dataset
uspto-grants-2011_02
Patent number
US07893073B2

Reaction notes

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