Toluene → HCID 15411299, compound

HRID 1292152Notes

Reaction equation

HRID 1292152 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][O:12][C:13]1[CH:14]=[C:15]([CH:31]=[CH:32][CH:33]=1)[CH2:16][O:17][C:18]1[CH:26]=[CH:25][C:24]([CH3:27])=[C:23]2[C:19]=1[C:20]([CH3:30])([CH3:29])[C:21](=O)[NH:22]2.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:43])=CC=1.C1(C)C=CC=CC=1>C(Cl)(Cl)Cl>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][O:12][C:13]1[CH:14]=[C:15]([CH:31]=[CH:32][CH:33]=1)[CH2:16][O:17][C:18]1[CH:26]=[CH:25][C:24]([CH3:27])=[C:23]2[C:19]=1[C:20]([CH3:30])([CH3:29])[C:21](=[S:43])[NH:22]2

Participants

5

Reactant 3

HCID 1140TolueneHCID 87949Lawesson's reagentHCID 19369479HCID 19369479, compound

Product 1

HCID 15411299HCID 15411299, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
100 °C

Procedure

To 1.189 g (2.71 mmol) of the 4-[3-(2-quinolinylmethoxy)benzyloxy]-3,3,7-trimethyl-2,3-dihydro-1H-indol-2-one obtained in Example 13, 1.076 g (2.71 mmol) of the Lawesson's reagent and 10 ml of toluene were added, followed by stirring at a bath temperature of 100° C. for 3 hours. After CHCl3 was added to dissolve the insoluble matter, the resulting solution was subjected to chromatography on a silica gel column. Subsequent to elution with CHCl3, recrystallization was conducted from AcOEt, whereby 678 mg of the title compound were obtained as pale yellow powder (yield: 55.0%).

Workup

  1. dissolutionto dissolve the insoluble matter
  2. washSubsequent to elution
  3. customwith CHCl3, recrystallization

Sources & evidence

ORD record
ord-35ab21fec0d04c0bb950de15ed919d3c
Source dataset
uspto-grants-1998_05
Patent number
US05756518

Reaction notes

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