Water → N-[(4-Methoxyphenyl)methyl]ethenesulfonamide

HRID 2231861Notes

Reaction equation

HRID 2231861 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][NH2:8])=[CH:5][CH:4]=1.C(N(CC)CC)C.Cl[CH2:19][CH2:20][S:21](Cl)(=[O:23])=[O:22].O>ClCCl>[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][NH:8][S:21]([CH:20]=[CH2:19])(=[O:23])=[O:22])=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 15385Ethanesulfonylchloride, 2-chloro-HCID 754524-Methoxybenzylamine

Product 1

HCID 13691361N-[(4-Methoxyphenyl)methyl]ethenesulfonamideYield 60.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A cold solution of 4-methoxybenzylamine (2 g) and triethylamine (2.8 ml) in dry dichloromethane (20 ml) at -78° was transferred under nitrogen to a solution of 2-chloroethanesulphonyl chloride (4.9 g) in dry dichloromethane (20 ml) at -78°. The mixture was stirred for 4 h whilst warming to room temperature and then refrigerated overnight. Water (ca 100 ml) was added and the organic layer separated. This was washed with hydrochloric acid (2N, 50 ml), water (50 ml) and brine (50 ml), dried (MgSO4) and evaporated under reduced pressure. The residue was purified by chromatography (dichloromethane) to give the title compound as a powder (2 g) m.p. 68°-69°.

Workup

  1. customat -78°
  2. customrefrigerated overnight
  3. customthe organic layer separated
  4. washThis was washed with hydrochloric acid (2N, 50 ml), water (50 ml) and brine (50 ml)
  5. dry with materialdried (MgSO4)
  6. customevaporated under reduced pressure
  7. customThe residue was purified by chromatography (dichloromethane)

Sources & evidence

ORD record
ord-387ca022414845dbbc563dde0d2d4441
Source dataset
uspto-grants-1988_11
Patent number
US04785016

Reaction notes

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