Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → 4-Hydroxy-4,5,6,7-tetrahydrobenzo[b]-thiophene-2-sulfonamide
Reaction equation
O1CCCCC1[O:7][CH:8]1[C:16]2[CH:15]=[C:14]([S:17]([NH2:20])(=[O:19])=[O:18])[S:13][C:12]=2[CH2:11][CH2:10][CH2:9]1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>C(O)C>[OH:7][CH:8]1[C:16]2[CH:15]=[C:14]([S:17]([NH2:20])(=[O:19])=[O:18])[S:13][C:12]=2[CH2:11][CH2:10][CH2:9]1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 55 °C
Procedure
To a solution of thoroughly dried product from Step C (5.9 g, 0.98 mol) in 140 ml absolute ethanol (warming necessary to promote solubility) was added 467 mg (0.0018 mol) pyridinium 4-toluenesulfonate (PPTS). After stirring under N2 at 55° C. for 3 hours, no reaction was detected by TLC. The solvent was removed under reduced pressure. Then, 125 ml absolute ethanol was added and PPTS was added until pH 3 was achieved. After 4 hours under N2 at 55° C. the solvent was removed under reduced pressure. The residue was chromatographed on silica gel first with 85:15 CHCl3 :CH3OH (v:v) and a second time with 90:10 CHCl3 :CH3OH (v:v) saturated with NH3. The product was recrystallized from H2O after decolorizing with charcoal, yielding 700 mg (17%) of product mp 102°-103° C.
Workup
- customThe solvent was removed under reduced pressure
- additionThen, 125 ml absolute ethanol was added
- additionPPTS was added until pH 3
- customAfter 4 hours under N2 at 55° C. the solvent was removed under reduced pressure
- customThe residue was chromatographed on silica gel first with 85:15 CHCl3
- customThe product was recrystallized from H2O
Sources & evidence
- ORD record
- ord-734e5fb2897b4092afdec9143e3d3448
- Source dataset
- uspto-grants-1987_06
- Patent number
- US04677115
Reaction notes
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