Potassium Carbonate → Methanesulfonamide, N-(2,4-dichlorophenyl)-N-(3-pyridinylmethyl)-

HRID 2351963Notes

Reaction equation

HRID 2351963 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[NH:9][CH2:10][C:11]1[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=1.[CH3:17][S:18](Cl)(=[O:20])=[O:19].C(=O)([O-])[O-].[K+].[K+]>ClCCl>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[N:9]([CH2:10][C:11]1[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=1)[S:18]([CH3:17])(=[O:20])=[O:19]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 31297Methanesulfonyl chlorideHCID 28045112,4-dichloro-N-(pyridin-3-ylmethyl)aniline

Product 1

HCID 188726Methanesulfonamide, N-(2,4-dichlorophenyl)-N-(3-pyridinylmethyl)-

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 2.7 g. portion of 3-(2,4-dichlorophenylaminomethyl)pyridine was dissolved in dichloromethane and reacted with 0.9 ml. of methanesulfonyl chloride in the presence of 1.4 g. of potassium carbonate at ambient temperature for several days. The reaction mixture was worked up as described in Example 4 to obtain 3.2 g. of oil, which was triturated with petroleum ether and then diethyl ether and filtered to obtain 2.8 g. of solid. The solid was triturated with chloroform, filtered and dried to obtain 0.9 g. of the desired product, m.p. 180°-186°. Its elemental analysis was as follows.

Workup

  1. customreacted with 0.9 ml
  2. customto obtain 3.2 g
  3. customof oil, which was triturated with petroleum ether
  4. filtrationdiethyl ether and filtered
  5. customto obtain 2.8 g
  6. customThe solid was triturated with chloroform
  7. filtrationfiltered
  8. customdried
  9. customto obtain 0.9 g

Sources & evidence

ORD record
ord-7dfde6a898344f9a80f30b53be45d078
Source dataset
uspto-grants-1989_10
Patent number
US04874775

Reaction notes

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