Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → HCID 22601708, compound

HRID 2308250Notes

Reaction equation

HRID 2308250 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]2[C:13]([CH3:14])=[C:12]([C:15]3[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=3)[S:11][C:10]=2[CH:23]2OCC[O:24]2)[CH:6]=[CH:7][CH:8]=1.CC1C=CC(S([O-])(=O)=O)=CC=1.C1C=C[NH+]=CC=1>CC(C)=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]2[C:13]([CH3:14])=[C:12]([C:15]3[CH:16]=[CH:17][C:18]([O:21][CH3:22])=[CH:19][CH:20]=3)[S:11][C:10]=2[CH:23]=[O:24])[CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 22601722HCID 22601722, compound

Product 1

HCID 22601708HCID 22601708, compoundYield 96.9%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

2-[3-(3-Methoxyphenyl)-5-(4-methoxyphenyl)-4-methylthien-2-yl]-1,3-dioxolane (7.0 g, 18 mmol) and PPTS (1.4 g, 5.6 mmol) were combined in wet acetone (180 mL) and heated at reflux for 2 h. At this time, the cooled solution was concentrated in vacuo and the residue was taken up in ethyl acetate (200 mL). The organic phase was washed with saturated aqueous NaHCO3 and brine (200 mL each), dried (Na2SO4) and concentrated in vacuo to give the title compound (5.9 g, 95%, m.p. 105-08° C.) as a yellow solid.

Workup

  1. temperatureheated
  2. temperatureat reflux for 2 h
  3. concentrationAt this time, the cooled solution was concentrated in vacuo
  4. washThe organic phase was washed with saturated aqueous NaHCO3 and brine (200 mL each)
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7ed3ede3fac34350988f671974a26225
Source dataset
uspto-grants-2004_12
Patent number
US06835745B2

Reaction notes

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