Sodium Hydroxide → HCID 19866589, compound

HRID 1199389Notes

Reaction equation

HRID 1199389 reaction equation
C([O:3][C:4](=[O:33])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][S:15][C:16]1[NH:17][C:18]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[C:19]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[N:20]=1)C.[OH-].[Na+]>C(O)C.O>[C:27]1([C:18]2[N:17]=[C:16]([S:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][C:4]([OH:33])=[O:3])[NH:20][C:19]=2[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 23220722HCID 23220722, compound

Product 1

HCID 19866589HCID 19866589, compoundYield 69.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of 6.0 g (0.013 mole) 11-(4,5-diphenyl-1H-imidazole-2-ylthio)undecanoic acid ethyl ester in 150 ml ethanol was added, dropwise, a solution of 6.0 g sodium hydroxide in 150 ml water. The reaction mixture was stirred at reflux under nitrogen for 3 hours. The solvent was concentrated to half the volume and the remaining solution was extracted with diethyl ether. This organic layer was discarded. The aqueous layer was acidified to pH=1.0 using 1N hydrochloric acid and then extracted with diethyl ether. The organic layer was dried over magnesium sulfate and the solvent removed under vacuum. The resulting solid was recrystallized from methanol and triturated with diethyl ether to give 4.10 g (0.009 mole) of the title compound as a white solid, mp=193°-195° C. 1HNMR(DMSO-d6): δ12.6(s,1H), 7.6-7.1(m,10H), 3.6(t,2H,J=7Hz), 2.3(t,2H,J=7Hz), 1.8-1.1(m,17H).

Workup

  1. temperatureat reflux under nitrogen for 3 hours
  2. concentrationThe solvent was concentrated to half the volume
  3. extractionthe remaining solution was extracted with diethyl ether
  4. extractionextracted with diethyl ether
  5. dry with materialThe organic layer was dried over magnesium sulfate
  6. customthe solvent removed under vacuum
  7. customThe resulting solid was recrystallized from methanol
  8. customtriturated with diethyl ether

Sources & evidence

ORD record
ord-8505bc0227aa4d53831819569cdd34a4
Source dataset
uspto-grants-1990_02
Patent number
US04900744

Reaction notes

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