Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → HCID 70143653, compound

HRID 1281693Notes

Reaction equation

HRID 1281693 reaction equation
C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.[Cl:18][C:19]1[C:38]([Cl:39])=[CH:37][C:22]2[N:23]([CH:26]3[CH2:36][CH2:35][CH:29]4[O:30]C(C)(C)[O:32][CH:28]4[CH2:27]3)[CH:24]=[N:25][C:21]=2[CH:20]=1>CO>[Cl:18][C:19]1[C:38]([Cl:39])=[CH:37][C:22]2[N:23]([C@@H:26]3[CH2:36][CH2:35][C@@H:29]([OH:30])[C@@H:28]([OH:32])[CH2:27]3)[CH:24]=[N:25][C:21]=2[CH:20]=1

Participants

4

Reactant 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 18422012HCID 18422012, compound

Product 1

HCID 70143653HCID 70143653, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Pyridinium para-toluenesulfonate (33.6 mg, 134.7 mmol) was added to (±)-5,6-dichloro-1-(2,2dimethyl-hexahydro-benzo[1,3]dioxol-5-yl)-1H-benzimidazole (part d of this experiment, 459.6 mg, 1.35 mmol) in methanol (7 ml) and the reaction was heated at reflux for 19 hr and concentrated. The residue was purified by column chromatography eluting with methanol:ethyl acetate (1:9) to give the title compound (184.4 mg, 45%). Rf=0.19 (1:9 methanol:ethyl acetate); 1H-NMR (CD3OD, 300 MHz) δ8.36 (s, 1H), 7.91 (s, 1H), 7.80 (s, 1H), 4.70 (tt, 1H, J=12, 4), 4.11 (d, 1H, J=3), 3.79-3.73 (m, 1H), 2.26 (dq, 1H, J=13, 3), 2.15-2.10 (m, 2H), 2.06-1.99 (m, 2H), 1.88-1.85 (m, 1H); MS (ES) M+H=301.

Workup

  1. temperaturethe reaction was heated
  2. temperatureat reflux for 19 hr
  3. concentrationconcentrated
  4. customThe residue was purified by column chromatography
  5. washeluting with methanol:ethyl acetate (1:9)

Sources & evidence

ORD record
ord-3c7992c0ac294ea6bdff376c9b49bc2b
Source dataset
uspto-grants-2002_09
Patent number
US06455507B1

Reaction notes

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