Dimethyl Sulfoxide → HCID 14664362, compound

HRID 1381911Notes

Reaction equation

HRID 1381911 reaction equation
[CH2:1]([N:3]([CH2:26][CH3:27])[CH2:4][CH2:5][N:6]([C:16]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:19]=[CH:18][CH:17]=1)[C:7](=[O:15])[C:8]1[CH:13]=[CH:12][C:11](F)=[CH:10][CH:9]=1)[CH3:2].[NH:28]1[CH:32]=[CH:31][N:30]=[CH:29]1.C(=O)([O-])[O-].[K+].[K+].CS(C)=O>O.CO.C(Cl)Cl>[CH2:1]([N:3]([CH2:26][CH3:27])[CH2:4][CH2:5][N:6]([C:16]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:19]=[CH:18][CH:17]=1)[C:7](=[O:15])[C:8]1[CH:13]=[CH:12][C:11]([N:28]2[CH:32]=[CH:31][N:30]=[CH:29]2)=[CH:10][CH:9]=1)[CH3:2]

Participants

8

Reactant 4

HCID 679Dimethyl SulfoxideHCID 795ImidazoleHCID 11430Potassium CarbonateHCID 14664361HCID 14664361, compound

Product 1

HCID 14664362HCID 14664362, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 6.0 g (16.5 mmol) N-[2-(diethylamino)ethyl]-4-fluoro-N-(1-naphthalenyl)benzamide, 1.68 g (24.7 mmol) of imidazole, 4.55 g (33 mmol) of anhydrous potassium carbonate and 6.0 mL of dimethylsulfoxide is heated to 150° C. for 18 hr. After this time, the reaction mixture is dissolved in 150 mL water, 100 mL methylene chloride and 40 mL of methanol. The organic is dried over sodium sulfate, filtered and the solvent distilled in vacuo. The residue is recrystallized from acetone to provide the title compound.

Workup

  1. dry with materialThe organic is dried over sodium sulfate
  2. filtrationfiltered
  3. distillationthe solvent distilled in vacuo
  4. customThe residue is recrystallized from acetone

Sources & evidence

ORD record
ord-5cce5c37e36b4f2a99da7e81a3de18b9
Source dataset
uspto-grants-1989_02
Patent number
US04804662

Reaction notes

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