4-Toluenesulfonyl chloride → HCID 59773380, compound

HRID 2114292Notes

Reaction equation

HRID 2114292 reaction equation
[C:1]1([C:7]2[NH:8][C:9]3[CH:15]=[C:14]([CH2:16][CH2:17][OH:18])[CH:13]=[CH:12][C:10]=3[N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[S:19](Cl)([C:22]1[CH:28]=[CH:27][C:25]([CH3:26])=[CH:24][CH:23]=1)(=[O:21])=[O:20]>N1C=CC=CC=1>[C:1]1([C:7]2[NH:8][C:9]3[CH:15]=[C:14]([CH2:16][CH2:17][O:18][S:19]([C:22]4[CH:28]=[CH:27][C:25]([CH3:26])=[CH:24][CH:23]=4)(=[O:21])=[O:20])[CH:13]=[CH:12][C:10]=3[N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 59773411HCID 59773411, compound

Product 1

HCID 59773380HCID 59773380, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Benzimidazole 190 (50 mg) was dissolved in pyridine (5 mL) and tosyl chloride (40 mg) was added as a solid. The reaction was allowed to stir for 16 h under nitrogen at room temperature before being quenched by addition of a saturated, aqueous solution of NH4Cl. This mixture was extracted with EtOAc which was in turn washed with dilute acid to ensure complete removal of pyridine. The organic layer was separated, dried over Na2SO4, and solvent removed under reduced pressure to give 191 which was used directly without further purification.

Workup

  1. custombefore being quenched by addition of a saturated, aqueous solution of NH4Cl
  2. extractionThis mixture was extracted with EtOAc which
  3. washwashed
  4. additionwith dilute acid
  5. customremoval of pyridine
  6. customThe organic layer was separated
  7. dry with materialdried over Na2SO4, and solvent
  8. customremoved under reduced pressure

Sources & evidence

ORD record
ord-5e342c0a114a4ff1b641ea89a236c5b2
Source dataset
uspto-grants-2008_10
Patent number
US07432379B2

Reaction notes

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