4-Toluenesulfonyl chloride → HCID 23365475, compound

HRID 1080721Notes

Reaction equation

HRID 1080721 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[NH:9][CH:10]=[CH:11][N:12]=1.C(N(CC)CC)C.[C:20]1([CH3:30])[CH:25]=[CH:24][C:23]([S:26](Cl)(=[O:28])=[O:27])=[CH:22][CH:21]=1>C(Cl)Cl.CN(C)C1C=CN=CC=1>[C:20]1([CH3:30])[CH:25]=[CH:24][C:23]([S:26]([N:12]2[CH:11]=[CH:10][N:9]=[C:8]2[C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[Br:1])(=[O:28])=[O:27])=[CH:22][CH:21]=1

Participants

6

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 100594482-(2-bromophenyl)-1H-imidazole

Product 1

HCID 23365475HCID 23365475, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of 2.50 g (11.6 mmol ) of 2-(2-bromophenyl)imidazole in 10 mL of methylene chloride was treated with 1.9 mL of triethylamine (13.8 mmol), 2.64 g (13.8 mmol) of p-toluenesulfonyl chloride and 100 mg of 4-dimethylaminopyridine. The reaction mixture was stirred at room temperature for 15 minutes then transferred to a separatory funnel and washed with water, 5% aqueous citric acid, saturated aqueous sodium bicarbonate and saturated aqueous sodium chloride. The organic layer was removed, dried over magnesium sulfate, filtered and solvents removed under vacuum. The crude product was chromatographed on silica, eluting with hexane/ethyl acetate (1:1), to give 4.16 g (11.0 mmol 95%) of the product which was recrystallized from hexane. FAB-MS: calculated for C16H13BrN2O2S 376,378; found 377,379 (M+H, 50%). 1H NMR (200 MHz, CDCl3): 2.32 (s, 3H), 7.09 (d, 2 Hz, 1H), 7.12 (d, 8 Hz, 2H), 7.28 (m, 5H), 7.46 (m, 1H), 7.57 (d, 2 Hz, 1H).

Workup

  1. customthen transferred to a separatory funnel
  2. washwashed with water, 5% aqueous citric acid, saturated aqueous sodium bicarbonate and saturated aqueous sodium chloride
  3. customThe organic layer was removed
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customsolvents removed under vacuum
  7. customThe crude product was chromatographed on silica
  8. washeluting with hexane/ethyl acetate (1:1)
  9. customto give 4.16 g (11.0 mmol 95%) of the product which
  10. customwas recrystallized from hexane

Sources & evidence

ORD record
ord-5fb88473a70f4857b7b0728e39144f58
Source dataset
uspto-grants-1996_12
Patent number
US05583130

Reaction notes

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