Sodium Hydroxide → HCID 22916338, compound

HRID 1199388Notes

Reaction equation

HRID 1199388 reaction equation
C([O:3][C:4](=[O:30])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][S:12][C:13]1[NH:14][C:15]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[C:16]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[N:17]=1)C.[OH-].[Na+]>C(O)C.O>[C:24]1([C:15]2[N:14]=[C:13]([S:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][C:4]([OH:30])=[O:3])[NH:17][C:16]=2[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 23220721HCID 23220721, compound

Product 1

HCID 22916338HCID 22916338, compoundYield 41.7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of 5.0 g (0.012 mole) 8-(4,5-diphenyl-1H-imidazol-2-ylthio)octanoic acid ethyl ester in 125 ml ethanol was added, dropwise, a solution of 5.0 g sodium hydroxide in 125 ml water. The reaction mixture was stirred at reflux under nitrogen for 4 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 crystallized from ethanol and triturated with hexane to give 2.13 g (0.005 mole) of the title compound as a white solid, mp=160°-162° C. 1H NMR(DMSO-d6): δ12.7(s,1H), 12.0(s,1H), 7.6-7.1(m,10H), 3.1(t,2H,J=7Hz), 2.3(t,2H,J=7Hz), 1.8-1.2 (m,10H).

Workup

  1. temperatureat reflux under nitrogen for 4 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 crystallized from ethanol
  8. customtriturated with hexane

Sources & evidence

ORD record
ord-a943b6c9d7754922a45b585a56fc8619
Source dataset
uspto-grants-1990_02
Patent number
US04900744

Reaction notes

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