Hydrochloric Acid → N-Allyl-4-methylbenzenesulfonamide

HRID 515912Notes

Reaction equation

HRID 515912 reaction equation
[CH2:1]([NH2:4])[CH:2]=[CH2:3].[S:5](Cl)([C:8]1[CH:14]=[CH:13][C:11]([CH3:12])=[CH:10][CH:9]=1)(=[O:7])=[O:6].C(N(CC)CC)C.Cl>ClCCl>[CH3:12][C:11]1[CH:13]=[CH:14][C:8]([S:5]([NH:4][CH2:1][CH:2]=[CH2:3])(=[O:7])=[O:6])=[CH:9][CH:10]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 73974-Toluenesulfonyl chlorideHCID 7853AllylamineHCID 8471Triethylamine

Product 1

HCID 297877N-Allyl-4-methylbenzenesulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Allylamine (10.6 mL, 0.14 mol) is added over a period of 4 minutes to a solution of tosyl chloride (25.1 g, 0.13 mol) in dichloromethane (250 mL) cooled in an ice bath. Triethylamine (24 mL, 0.18 mol) is added and then the solution is stirred at ambient temperature for 1.25 hours. Aqueous 3N HCl solution (60 mL) is added and the phases are then separated. The organic phase is washed with another amount of aqueous 3N HCl solution (60 mL) and then with 5% aqueous sodium bicarbonate solution (60 mL). The organic phase is dried over Na2SO4, filtered and concentrated to obtain the expected compound in the form of a solid.

Workup

  1. temperaturecooled in an ice bath
  2. customthe phases are then separated
  3. washThe organic phase is washed with another amount of aqueous 3N HCl solution (60 mL)
  4. dry with materialThe organic phase is dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-a354da6b8eb0486880d8e06bf45261ac
Source dataset
uspto-grants-2015_08
Patent number
US09108983B2

Reaction notes

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