Methanesulfonic Acid → 6-Methoxy-2-(4-methoxyphenyl)benzo[b]thiophene

HRID 1638128Notes

Reaction equation

HRID 1638128 reaction equation
[C:1]1([C:9]([CH:11]([C:13]2[CH:20]=[CH:19][C:16]([O:17][CH3:18])=[CH:15][CH:14]=2)O)=O)[CH:8]=[CH:7][C:4]([O:5][CH3:6])=[CH:3][CH:2]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:30])=CC=1.CS(O)(=O)=O>ClC1C=CC=CC=1>[CH3:6][O:5][C:4]1[CH:7]=[CH:8][C:1]([C:9]2[S:30][C:14]3[CH:15]=[C:16]([O:17][CH3:18])[CH:19]=[CH:20][C:13]=3[CH:11]=2)=[CH:2][CH:3]=1

Participants

5

Reactant 3

HCID 6395Methanesulfonic AcidHCID 87949Lawesson's reagentHCID 954154,4'-Dimethoxybenzoin

Product 1

HCID 8509416-Methoxy-2-(4-methoxyphenyl)benzo[b]thiopheneYield 10%

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Conditions

Temperature
100 °C

Procedure

Anisoin (2.87 g), 50 ml of chlorobenzene, and Lawesson's Reagent 4.04 g are placed in a flask under nitrogen. The mixture is heated to 100° C. and a methanesulfonic acid (0.65 mL) is added and the mixture heated at reflux for 92 hours. The reaction is cooled to room temperature before filtering the solids which form. The filter cake is washed with 25 ml of chlorobenzene and dried to give 270 mg of product. The solid is recrystallized from hot chlorobenzene to give 90 mgs of pure product. Analysis calculated for C16H14O4S: C, 71.08; H, 5.22; S, 11.86. Found: C, 71.27; H, 5.43; S, 11.78. MS.

Workup

  1. temperaturethe mixture heated
  2. temperatureat reflux for 92 hours
  3. temperatureThe reaction is cooled to room temperature
  4. filtrationbefore filtering the solids which
  5. customform
  6. washThe filter cake is washed with 25 ml of chlorobenzene
  7. customdried

Sources & evidence

ORD record
ord-74fac657aa444fb187fb625276aea729
Source dataset
uspto-grants-2000_03
Patent number
US06043360

Reaction notes

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