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Sodium ethoxide → HCID 178505574, compound

HRID 2117732
Notes
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Reaction equation

HRID 2117732 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([C:14]3[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=3)=[N:10][C:11](=[S:13])[N:12]=2)=[CH:4][CH:3]=1.[O-]CC.[Na+]>CO>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[NH:12][C:11]([SH:13])=[N:10][C:9]=2[C:14]2[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=2)=[CH:6][CH:7]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 2723922Sodium ethoxideHCID 18461195HCID 18461195, compound

Product 1

HCID 178505574HCID 178505574, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Under an atmosphere of argon, 5-(4-fluorophenyl)-4-(4-pyridinyl)imidazole-2-thione (0.001 mol/0.271 g) was dissolved in 20 ml of absolute methanol. Sodium ethoxide (0.0012 mol/0.065 g) was then added and the mixture was stirred for 10 min. The bromoaliphatic compound (0.0011 mol) in question, dissolved in 10 ml of absolute methanol, was added dropwise to the initial charge. The mixture was then heated under reflux for 4 h and subsequently stirred at room temperature for 2 h. After neutralization with HCl 10% to pH 7, the liquid was removed under reduced pressure and the residue was worked up by column chromatography (mobile phase: CH2Cl2/EtOH 9:1; silica gel).

Workup

  1. additionwas added dropwise to the
  2. additioninitial charge
  3. temperatureThe mixture was then heated
  4. temperatureunder reflux for 4 h
  5. stirringsubsequently stirred at room temperature for 2 h
  6. customAfter neutralization with HCl 10% to pH 7, the liquid was removed under reduced pressure

Sources & evidence

ORD record
ord-9f04684da3784c6ba56352e6e88d5056
Source dataset
uspto-grants-2008_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07442713B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes