Dimethylformamide → HCID 58674265, compound

HRID 2246400Notes

Reaction equation

HRID 2246400 reaction equation
[F:1][C:2]([F:14])([F:13])[C:3]1[CH:4]=[C:5]([NH:9][C:10]([NH2:12])=[O:11])[CH:6]=[CH:7][CH:8]=1.[N+:15]([C:18]1[CH:19]=[C:20]([CH:23]=[CH:24][CH:25]=1)[CH:21]=O)([O-:17])=[O:16].O=[C:27]([CH3:34])[CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30].CN(C=O)C>O1CCOCC1>[CH3:34][C:27]1[N:9]([C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:13])([F:14])[F:1])[CH:4]=2)[C:10](=[O:11])[NH:12][CH:21]([C:20]2[CH:23]=[CH:24][CH:25]=[C:18]([N+:15]([O-:17])=[O:16])[CH:19]=2)[C:28]=1[C:29]([O:31][CH2:32][CH3:33])=[O:30]

Participants

6

Reactant 4

HCID 6228Dimethylformamide2×HCID 74493-NitrobenzaldehydeHCID 8868Ethyl AcetoacetateHCID 25712(3-Trifluoromethylphenyl)urea

Product 1

HCID 58674265HCID 58674265, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

30.6 mg (0.15 mmol) N-[3-(trifluoromethyl)phenyl]urea are shaken together with 45.3 mg (0.3 mmol) 3-nitrobenzaldehyde, 39 mg (0.3 mmol) ethyl 3-oxobutanoate and 90 mg polyphosphoric acid ethyl ester [freshly prepared according to the procedure of Cava et al., J. Org. Chem. 34, 2665 (1969)] in 0.5 ml dioxan and 0.1 ml DMF at 80° C. for 18 hours. After adding 200 μl DMF, the reaction mixture is filtered and purified by preparative HPLC (column: Nucleosil 100-5 C 18 Nautilus 20 mm×50 mm, 5 μm; solvent A: acetonitrile, solvent B: water+0.1% formic acid; gradient: 0 min 10% A, 2 min 10% A, 6 min 90% A, 7 min 90% A, 7.1 min 10% A, 8 min 10% A; flow rate 25 ml/min; wavelength: 220 nm; injection volume: approx. 800 μl; number of injections: 1). The product containing fractions are combined and concentrated in vacuo.

Workup

  1. customfreshly prepared
  2. filtrationthe reaction mixture is filtered
  3. custompurified by preparative HPLC (column: Nucleosil 100-5 C 18 Nautilus 20 mm×50 mm, 5 μm; solvent A: acetonitrile, solvent B: water+0.1% formic acid; gradient: 0 min 10% A, 2 min 10% A, 6 min 90% A, 7 min 90% A, 7.1 min 10% A, 8 min 10% A; flow rate 25 ml/min; wavelength: 220 nm; injection volume: approx. 800 μl; number of injections: 1)
  4. additionThe product containing fractions
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-76763cc5b2964a949bb6ee8989e08159
Source dataset
uspto-grants-2010_03
Patent number
US07687510B2

Reaction notes

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