p-Toluenesulfonic acid monohydrate → HCID 20251885, compound

HRID 1284482Notes

Reaction equation

HRID 1284482 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][C:5]([NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[NH:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=O.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1.ClCCl>[Cl:1][CH2:2][CH2:3][CH2:4][C:5]1[N:14]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[N:7]=1

Participants

5

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 20251875HCID 20251875, compound

Product 1

HCID 20251885HCID 20251885, compoundYield 31.6%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 4-chloro-N-(2-anilinophenyl)butyramide (0.5 g) and p-toluenesulfonic acid monohydrate (33 mg) in toluene (15 ml) was refluxed for 1.5 hours. Toluene was removed under reduced pressure to afford a residue, which was dissolved in dichloromethane (20 ml), washed with a saturated aqueous solution of sodium bicarbonate and water in turn and dried over magnesium sulfate. Removal of the solvent under reduced pressure afforded an oily residue, which was subjected to column chromatography on silica gel (5 g) eluting with a mixture of dichloromethane and ethyl acetate (10:1) to give crystals of 2-(3-chloropropyl)-1-phenyl-1H-benzimidazole (148 mg).

Workup

  1. customToluene was removed under reduced pressure
  2. customto afford a residue, which
  3. washwashed with a saturated aqueous solution of sodium bicarbonate and water in turn
  4. dry with materialdried over magnesium sulfate
  5. customRemoval of the solvent under reduced pressure
  6. customafforded an oily residue, which
  7. washeluting with a mixture of dichloromethane and ethyl acetate (10:1)

Sources & evidence

ORD record
ord-1b3f1c63ab654065990041853a9f594f
Source dataset
uspto-grants-1986_01
Patent number
US04563455

Reaction notes

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