Thiophenol → HCID 66596910, compound

HRID 504017Notes

Reaction equation

HRID 504017 reaction equation
ClC[C:3]1[CH:25]=[CH:24][C:6]([CH2:7][N:8]2[C:17]3[C:12](=[C:13]([CH:18]4[O:22][CH2:21][CH2:20][O:19]4)[CH:14]=[CH:15][CH:16]=3)[CH2:11][CH2:10][C:9]2=[O:23])=[CH:5][CH:4]=1.[C:26]1([SH:32])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>C1COCC1>[O:19]1[CH2:20][CH2:21][O:22][CH:18]1[C:13]1[CH:14]=[CH:15][CH:16]=[C:17]2[C:12]=1[CH2:11][CH2:10][C:9](=[O:23])[N:8]2[CH2:7][C:6]1[CH:24]=[CH:25][C:3]([S:32][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[CH:4][CH:5]=1

Participants

4

Reactant 2

HCID 7969ThiophenolHCID 66596909HCID 66596909, compound

Product 1

HCID 66596910HCID 66596910, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-(4-Chloromethylbenzyl)-5-(1,3-dioxolan-2-yl)-3,4-dihydro-1H-quinolin-2-one (1.0 g, 2.79 mmol), thiophenol (0.37 ml, 3.63 mmol) and 1,8-diazabicyclo[5.4.0]undecene-7 (DBU) (0.84 ml, 5.59 mmol) were added to THF (30 ml), followed by heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=1:1). The purified product was concentrated to dryness under reduced pressure to thereby obtain 1.13 g (yield: 94%) of 5-(1,3-dioxolan-2-yl)-1-(4-phenylsulfanylbenzyl)-3,4-dihydro-1H-quinolin-2-one as a white solid.

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 7 hours
  3. concentrationthe reaction mixture was concentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=1:1)
  5. concentrationThe purified product was concentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-d87951d2a7b14ae5bf4124d83c126edb
Source dataset
uspto-grants-2010_08
Patent number
US07777038B2

Reaction notes

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