p-Toluenesulfonic acid → HCID 14168443, compound

HRID 2072675Notes

Reaction equation

HRID 2072675 reaction equation
[CH3:1][NH:2][S:3]([C:6]1[S:10][C:9]2[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=2[C:7]=1[CH2:15][C:16]([OH:18])=O)(=[O:5])=[O:4].C1(C)C=CC(S(O)(=O)=O)=CC=1>>[CH3:1][N:2]1[C:16](=[O:18])[CH2:15][C:7]2[C:8]3[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=3[S:10][C:6]=2[S:3]1(=[O:5])=[O:4]

Participants

3

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 14168442HCID 14168442, compound

Product 1

HCID 14168443HCID 14168443, compoundYield 75.3%

Procedure

A solution of 2-[(Methylamino)sulfonyl]-benzo-[b]thiophene-3-acetic acid (450 mg, 1.58 mmoles) and p-toluenesulfonic acid (45 mg) in xylenes (100 ml) was refluxed in a Dean-Stark trap for 6 hours. The solvent was evaporated and the resulting solid recrystallized from isopropanol to give the title compound (318 mg) in a yield of 765, mp 175°-178° C.; ms:m/e 267 (m+,25), 210(8), 160(5), 146(100); 1H-nmr(deuteriochloroform): δ7.96 (m,1H), 7,80 (m,1H), 7.58 (m,2H), 4.22 (s,2H), 3.38 (5,3H); ir (potassium bromide): 1700 cm-1.

Workup

  1. customThe solvent was evaporated
  2. customthe resulting solid recrystallized from isopropanol

Sources & evidence

ORD record
ord-ace8c8e1843a43ddba5d4d2da8cc3966
Source dataset
uspto-grants-1990_04
Patent number
US04914101

Reaction notes

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