4-Toluenesulfonyl chloride → HCID 19001524, compound

HRID 2259648Notes

Reaction equation

HRID 2259648 reaction equation
[N+:1]([C:4]1[CH:21]=[CH:20][C:7]2[N:8]=[C:9]([NH:11][C:12](=O)[CH:13]3[CH2:18][CH2:17][NH:16]CC3)[S:10][C:6]=2[CH:5]=1)([O-:3])=[O:2].[C:22]1(C)C=CC(S(Cl)(=O)=O)=C[CH:23]=1.[OH-].[Na+]>CN(C)C=O>[N+:1]([C:4]1[CH:21]=[CH:20][C:7]2[N:8]=[C:9]([N:11]3[CH2:12][CH2:13][CH:18]([C:17]#[N:16])[CH2:23][CH2:22]3)[S:10][C:6]=2[CH:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 19001536HCID 19001536, compound

Product 1

HCID 19001524HCID 19001524, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

75 g of the N-(6-nitrobenzothiazol-2-yl)isonipecotamide obtained in the Preparation Example 12 was dissolved in 700 ml of dimethylformamide. 50 g of p-toluenesulfonoyl chloride was added to the solution and the mixture was heated at 110° C. for 20 min, poured into ice/water and neutralized with sodium hydroxide. The formed precipitates were recovered by filtration, washed with water and then with ether, and dried to give 60 g of the titled compound.

Workup

  1. customThe formed precipitates
  2. filtrationwere recovered by filtration
  3. washwashed with water
  4. dry with materialwith ether, and dried

Sources & evidence

ORD record
ord-375b89bc95984d07930d5ca07ae7d6cc
Source dataset
uspto-grants-1995_12
Patent number
US05475014

Reaction notes

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