Ethyl 8-bromooctanoate → HCID 23220721, compound

HRID 1199386Notes

Reaction equation

HRID 1199386 reaction equation
[C:1]1([C:7]2[N:8]=[C:9]([SH:18])[NH:10][C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:19]([O:21][C:22](=[O:31])[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29]Br)[CH3:20].C(=O)(O)[O-].[Na+]>CN(C)C=O>[CH2:19]([O:21][C:22](=[O:31])[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][S:18][C:9]1[NH:8][C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[C:11]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:10]=1)[CH3:20]

Participants

5

Reactant 3

HCID 264813Ethyl 8-bromooctanoateHCID 516892Sodium BicarbonateHCID 178527825HCID 178527825, compound

Product 1

HCID 23220721HCID 23220721, compoundYield 73.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 7.57 g (0.03 mole) 4,5-diphenyl-2-imidazolethiol in 75 ml dimethylformamide was added, dropwise, 7.23 g (0.03 mole) ethyl-8-bromooctanoate in 25 ml dimethylformamide. The reaction mixture was stirred at reflux under nitrogen overnight. The cooled solution was poured into 5% sodium bicarbonate and ice and then extracted with ethyl acetate. The organic layer was backwashed with 5% sodium bicarbonate, water, and saturated sodium chloride solution, then dried over magnesium sulfate and the solvent was removed under vacuum. The residue was chromatographed using hexane:ethyl acetate (7:3). The resulting solid was recrystallized from ethanol and triturated with hexane to give 9.12 g (0.022 mole) of the title compound as a white solid, mp=77°-79° C. H1NMR(DMSO-d6): δ12.6(s,1H), 7.7-7.1(m,10H), 4.0(q,2H,J=8Hz), 3.1(t,2H,J=7Hz), 2.3(t,2H,J=17Hz), 1.8-1.1(m,13H).

Workup

  1. temperatureat reflux under nitrogen overnight
  2. extractionextracted with ethyl acetate
  3. dry with materialdried over magnesium sulfate
  4. customthe solvent was removed under vacuum
  5. customThe residue was chromatographed
  6. customThe resulting solid was recrystallized from ethanol
  7. customtriturated with hexane

Sources & evidence

ORD record
ord-72ef84ff4693498aafd7c10d6cd5947c
Source dataset
uspto-grants-1990_02
Patent number
US04900744

Reaction notes

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