4-Toluenesulfonyl chloride → Thieno[2,3-c]pyridin-7-amine

HRID 376314Notes

Reaction equation

HRID 376314 reaction equation
[S:1]1[C:5]2=[CH:6][N+:7]([O-])=[CH:8][CH:9]=[C:4]2[CH:3]=[CH:2]1.C1(C)C=CC(S(Cl)(=O)=O)=CC=1.O.[NH3:23]>C(Cl)(Cl)Cl>[NH2:23][C:6]1[N:7]=[CH:8][CH:9]=[C:4]2[CH:3]=[CH:2][S:1][C:5]=12

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 12896473Azane;hydrateHCID 14666712thieno[2,3-c]pyridine-N-oxide

Product 1

HCID 23437721Thieno[2,3-c]pyridin-7-amine

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a solution of 16.6 g of thieno[2,3-c]pyridine-N-oxide in 500 ml of chloroform was added 25 g of p-toluenesulfonyl chloride portionwise with ice-cooling over a period of 1 hour. After the reaction mixture was stirred for further 30 minutes under the same conditions, 250 ml of 10% ammonia water was added, and stirred at ambient temperature for 16 hours. The reaction mixture was diluted with 400 ml of chloroform, washed with water and saturated saline, and dried over anhydrous magnesium sulfate. The drying agent was removed by filtration, and the solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel to give 2.8 g of the title compound as a brown oily material.

Workup

  1. temperaturecooling over a period of 1 hour
  2. additionwas added
  3. washwashed with water and saturated saline
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe drying agent was removed by filtration
  6. customthe solvent was removed under reduced pressure
  7. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-a6cbdac9a36042be9b1f7e2f9d16a6a0
Source dataset
uspto-grants-2000_02
Patent number
US06020342

Reaction notes

Loading…