Ethyl 11-bromoundecanoate → HCID 23220722, compound

HRID 1199387Notes

Reaction equation

HRID 1199387 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:34])[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32]Br)[CH3:20].C(=O)(O)[O-].[Na+]>CN(C)C=O>[CH2:19]([O:21][C:22](=[O:34])[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][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 235144Ethyl 11-bromoundecanoateHCID 516892Sodium BicarbonateHCID 178527825HCID 178527825, compound

Product 1

HCID 23220722HCID 23220722, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 12.6 g (0.05 mole) 4,5-diphenyl-2-imidazolethiol in 125 ml dimethylformamide was added, dropwise, 14.2 g (0.05 mole) ethyl-11-bromoundecanoate in 40 ml dimethylformamide and 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 (9:1). The resulting solid was triturated with hexane to give 13.58 g (0.029 mole) of the title compound as a white solid, mp=57°-59° C. 1HNMR(DMSO-d6): δ12.6(s,1H), 7.6-7.1(m,10H), 4.0(q,2H,J=8Hz), 3.5(t,2H,J=7Hz), 2.25(t,2H,J=7Hz), 1.8-1.1(m.21H).

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 triturated with hexane

Sources & evidence

ORD record
ord-364ce073024f448bba8d35e226807fe3
Source dataset
uspto-grants-1990_02
Patent number
US04900744

Reaction notes

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