2-Ethoxy-1-(ethoxycarbonyl)-1,2-dihydroquinoline → {5'-[8-(Benzoxazol-2-ylsulfanyl)-octylcarbamoyl]-3,3''-dichloro-[1,1':3'1'']-terphenyl-2'-yloxy}-ethanol

HRID 1281392Notes

Reaction equation

HRID 1281392 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[S:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][NH2:19].[Cl:20][C:21]1[CH:22]=[C:23]([C:27]2[CH:28]=[C:29]([CH:33]=[C:34]([C:40]3[CH:45]=[CH:44][CH:43]=[C:42]([Cl:46])[CH:41]=3)[C:35]=2[O:36]CCO)[C:30](O)=[O:31])[CH:24]=[CH:25][CH:26]=1.[CH3:47][CH2:48][O:49]C1N(C(OCC)=O)C2C(=CC=CC=2)C=C1>C1C=CC=CC=1.CCO.CCOC(C)=O>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[S:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][NH:19][C:30]([C:29]1[CH:33]=[C:34]([C:40]2[CH:45]=[CH:44][CH:43]=[C:42]([Cl:46])[CH:41]=2)[C:35]([O:36][CH:48]([OH:49])[CH3:47])=[C:27]([C:23]2[CH:24]=[CH:25][CH:26]=[C:21]([Cl:20])[CH:22]=2)[CH:28]=1)=[O:31]

Participants

6

Reactant 3

HCID 278332-Ethoxy-1-(ethoxycarbonyl)-1,2-dihydroquinolineHCID 222373953,5-Bis(3-chlorophenyl)-4-(2-hydroxyethoxy)benzoic acidHCID 222375188-(Benzoxazol-2-ylsulfanyl)octylamine

Product 1

HCID 86583658{5'-[8-(Benzoxazol-2-ylsulfanyl)-octylcarbamoyl]-3,3''-dichloro-[1,1':3'1'']-terphenyl-2'-yloxy}-ethanolYield 74.1%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 21965192Npc112006Solvent

Procedure

To a flame dried round bottom flask with 8-(benzoxazol-2-ylsulfanyl)octylamine (0.155 g, 0.558 mmol) in benzene:EtOH (1:1, 6 mL) at room temperature was added 3,5-bis-(m-chlorophenyl)-4-(2-hydroxyethoxy)benzoic acid (0.150 g, 0.372 mmol) followed by EEDQ (0.258 g, 1.04 mmol). After 3 days at this temperature, it was diluted with EtOAc (200 mL). This solution was washed with 1 N HCl (20 mL), sat. aq. NaHCO3 (20 mL), and brine (20 mL) and then dried (MgSO4). After concentration, the residue was purified by preparatory plate chromatography (30% EtOAc/petroleum ether) to afford the product (0.183 g, 74%) as a solid; 1H NMR (CDCl3) δ 1.28-1.42 (m, 6H), 1.42-1.68 (m, 5H), 1.77-1.97 (m, 2H), 3.27-3.41 (m, 6H), 3.46 (dd, J=6.1, 13.5 Hz, 2H), 6.09-6.17 (m, 1H), 7.22-7.47 (m, 7H), 7.47-7.54 (m, 2H), 7.54-7.66 (m, 3H), 7.74 (s, 2H); mass spectrum [(+) ESI], m/z 664 (M+H)+.

Workup

  1. washThis solution was washed with 1 N HCl (20 mL), sat. aq. NaHCO3 (20 mL), and brine (20 mL)
  2. dry with materialdried (MgSO4)
  3. concentrationAfter concentration
  4. customthe residue was purified by preparatory plate chromatography (30% EtOAc/petroleum ether)

Sources & evidence

ORD record
ord-1cce95a1e00e4ec9b864bac2bbc9082b
Source dataset
uspto-grants-2002_09
Patent number
US06451827B2

Reaction notes

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