Dimethyl Sulfoxide → HCID 58674272, compound

HRID 2246399Notes

Reaction equation

HRID 2246399 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]([NH2:12])=[O:11])[CH:5]=[C:6]([Cl:8])[CH:7]=1.[CH:13]([C:15]1[CH:22]=[CH:21][C:18]([C:19]#[N:20])=[CH:17][CH:16]=1)=O.O=[C:24]([CH3:31])[CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27].CS(C)=O>O1CCOCC1>[C:19]([C:18]1[CH:21]=[CH:22][C:15]([CH:13]2[C:25]([C:26]([O:28][CH2:29][CH3:30])=[O:27])=[C:24]([CH3:31])[N:9]([C:4]3[CH:3]=[C:2]([Cl:1])[CH:7]=[C:6]([Cl:8])[CH:5]=3)[C:10](=[O:11])[NH:12]2)=[CH:16][CH:17]=1)#[N:20]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8868Ethyl AcetoacetateHCID 660424-CyanobenzaldehydeHCID 41650041-(3,5-Dichlorophenyl)urea

Product 1

HCID 58674272HCID 58674272, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Under argon, 30.8 mg (0.15 mmol) N-(3,5-dichlorophenyl)urea are stirred together with 39.3 mg (0.3 mmol) 4-formylbenzonitrile, 39 mg (0.3 mmol) ethyl 3-oxo-butanoate and 90 mg trimethylsilylpolyphosphate in 0.5 ml dioxan at 80° C. for 4 hours. After adding a small amount of DMSO, the reaction mixture is filtered and purified by preparative HPLC (column: Agilent Zorbax Extend C18 20 mm×50 mm, 5 μm; solvent A: acetonitrile, solvent B: water+0.1% conc. aq. ammonia; 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. 500 μl; number of injections: 1). The product containing fractions are combined and concentrated in vacuo.

Workup

  1. filtrationthe reaction mixture is filtered
  2. custompurified by preparative HPLC (column: Agilent Zorbax Extend C18 20 mm×50 mm, 5 μm; solvent A: acetonitrile, solvent B: water+0.1% conc. aq. ammonia; 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. 500 μl; number of injections: 1)
  3. additionThe product containing fractions
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c94baa4cb69842718b655f7152888ae4
Source dataset
uspto-grants-2010_03
Patent number
US07687510B2

Reaction notes

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