Methanesulfonyl chloride → HCID 22203276, compound

HRID 2372640Notes

Reaction equation

HRID 2372640 reaction equation
[NH2:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[C:5]([O:11][CH3:12])[CH:4]=1.[CH3:13][S:14](Cl)(=[O:16])=[O:15]>ClCCl>[CH3:12][O:11][C:5]1[CH:4]=[C:3]([CH2:2][NH:1][S:14]([CH3:13])(=[O:16])=[O:15])[CH:8]=[CH:7][C:6]=1[O:9][CH3:10]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 79832Veratrylamine

Product 1

HCID 22203276HCID 22203276, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

1-(Aminomethyl)-3,4-dimethoxybenzene (18 ml., 120 mmole, 2 eq.) was added to a solution of methanesulfonyl chloride (4.64 ml., 60 mmole, 1 eq.) in dichloromethane (30 ml., 2.0M) at 0°. Additional dichloromethane (90 ml., final concentration of 0.5M) was then added. The reaction was allowed to warm to room temperature and stirred 2 days. The solid which had precipitated was filtered off and washed with additional dichloromethane. The filtrate was washed with 0.5N HCl (2×200 ml.) and water (200 ml.), dried (MgSO4), filtered, and concentrated to give 13.93 g. of yellow solid. This material was recrystallized from ethyl acetate:hexane (1:1, 75 ml.). The crystalline product was washed with ethyl acetate:hexane (1:1) and ether and dried to give 12.41 g. of N-[(3,4-dimethoxy)methyl]methanesulfonamide; m.p. 78°-81°.

Workup

  1. customThe solid which had precipitated
  2. filtrationwas filtered off
  3. washwashed with additional dichloromethane
  4. washThe filtrate was washed with 0.5N HCl (2×200 ml.) and water (200 ml.)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give 13.93 g
  9. customThis material was recrystallized from ethyl acetate:hexane (1:1, 75 ml.)
  10. washThe crystalline product was washed with ethyl acetate:hexane (1:1) and ether
  11. customdried
  12. customto give 12.41 g

Sources & evidence

ORD record
ord-f00436c8e76b408381b6a6e7bb7e7782
Source dataset
uspto-grants-1992_03
Patent number
US05098924

Reaction notes

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