4-Toluenesulfonyl chloride → HCID 14750491, compound

HRID 1091093Notes

Reaction equation

HRID 1091093 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([CH3:14])[N+:9]=2[O-])[CH:4]=1.C1(C)C=CC(S([Cl:24])(=O)=O)=CC=1>ClC(Cl)C>[Cl:24][CH2:14][C:8]1[CH:7]=[CH:6][C:5]2[C:10](=[CH:11][CH:12]=[C:3]([O:2][CH3:1])[CH:4]=2)[N:9]=1

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 15675919HCID 15675919, compound

Product 1

HCID 14750491HCID 14750491, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Conditions

Temperature
100 °C

Procedure

6-Methoxyquinaldine N-Oxide (6.94 g, 36.71 mmol) was added to a stirring solution of p-toluenesulfonylchloride (7.0 g, 36.84 mmol) in dichloroethane (100 mL). The reaction was heated to 100° C. overnight, partitioned between 10% K2CO3 /ethyl acetate, dried over MgSO4, and evaporated under reduced pressure. The crude solid was purified by HPLC to afford 2.6 g (37%) of chloride.

Workup

  1. custompartitioned between 10% K2CO3 /ethyl acetate
  2. dry with materialdried over MgSO4
  3. customevaporated under reduced pressure
  4. customThe crude solid was purified by HPLC

Sources & evidence

ORD record
ord-89381597ab3649818016828677a9e06f
Source dataset
uspto-grants-1992_01
Patent number
US05084463

Reaction notes

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