Methanesulfonyl chloride → HCID 131716175, compound

HRID 2351989Notes

Reaction equation

HRID 2351989 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F: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:21])(=[O:20])=[O:19]>ClCCl>[ClH:21].[F:1][C:2]1[CH:7]=[C:6]([F: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

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 110961292,4-difluoro-N-(pyridin-3-ylmethyl)aniline

Product 1

HCID 131716175HCID 131716175, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 11 g. portion of 3-(2,4-difluorophenylaminomethyl)pyridine was dissolved in 50 ml. of dichloromethane, and 4.6 ml. of methanesulfonyl chloride was added. The mixture was stirred at ambient temperature overnight. A solid had formed, which was filtered from the mixture. The filtrate was partially evaporated under vacuum, producing more solid which was removed and discarded. The filtrate was chromatographed over silica gel, eluting first with dichloromethane, then with dichloromethane:ethyl acetate, and finally with dichloromethane:methanol. The product-containing fractions were combined and evaporated to produce 1.9 g. of the desired product in the free base form. That product was dissolved in dichloromethane, with stirring, and hydrogen chloride was bubbled through the solution. Some solid formed. The mixture was diluted with 250 ml. of diethyl ether and filtered. The solids were washed with diethyl ether and dried under vacuum to obtain 2 g. of the desired product, m.p. 203°-206°.

Workup

  1. customA solid had formed
  2. filtrationwhich was filtered from the mixture
  3. customThe filtrate was partially evaporated under vacuum
  4. customproducing more solid which
  5. customwas removed
  6. customThe filtrate was chromatographed over silica gel
  7. washeluting first with dichloromethane
  8. customevaporated
  9. customto produce 1.9 g

Sources & evidence

ORD record
ord-3388855893c84e7a9ac26ffef2d11f6f
Source dataset
uspto-grants-1989_10
Patent number
US04874775

Reaction notes

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