Pyridine → HCID 68522192, compound

HRID 1992371Notes

Reaction equation

HRID 1992371 reaction equation
[Cl:1][CH2:2][CH2:3][S:4](Cl)(=[O:6])=[O:5].CS(O)(=O)=O.[NH2:13][CH2:14][C:15]1[CH:22]=[CH:21][C:18]([C:19]#[N:20])=[CH:17][CH:16]=1.N1C=CC=CC=1.C(C1C=CC(CNS(C=C)(=O)=O)=CC=1)#N>ClCCl>[C:14]([C:15]1[CH:22]=[CH:21][C:18]([CH2:19][NH:20][S:4]([CH2:3][CH2:2][Cl:1])(=[O:6])=[O:5])=[CH:17][CH:16]=1)#[N:13]

Participants

6

Reactant 4

HCID 1049PyridineHCID 15385Ethanesulfonylchloride, 2-chloro-HCID 9815996HCID 9815996, compoundHCID 86625994HCID 86625994, compound

Product 1

HCID 68522192HCID 68522192, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Chloroethane sulfonyl chloride (4.8 g, 0.029 mol) was added drop by drop to solution of 4-aminomethyl benzonitrile methan sulphonic acid salt acid (7 g, 0.029 mol) and pyridine (24 ml) in dry dichloromethane (25 ml) at −5° C. under nitrogen atmosphere. The reaction mixture was stirred at RT for 2 days and then partitioned between water and dichloromethane. The organic layer was washed with water and brine and dried over sodium sulfate. Solvent was evaporated under reduced pressure and the residue was purified by column chromatography over silica gel using 1% methanol in chloroform as eluent to give mixture of the sub-title compound and ethenesulfonic acid 4-cyano-benzylamide (3.4 g) as a solid. This was directly taken for next step without further purification.

Workup

  1. custompartitioned between water and dichloromethane
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over sodium sulfate
  4. customSolvent was evaporated under reduced pressure
  5. customthe residue was purified by column chromatography over silica gel using 1% methanol in chloroform as eluent
  6. customto give

Sources & evidence

ORD record
ord-16776ca9a06f48358d16b8f3c4de1781
Source dataset
uspto-grants-2010_01
Patent number
US07648985B2

Reaction notes

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