Allyl bromide → HCID 67414600, compound

HRID 2374694Notes

Reaction equation

HRID 2374694 reaction equation
C[NH:2][S:3]([C:6]1[CH:11]=[CH:10][C:9]([CH3:12])=[CH:8][CH:7]=1)(=[O:5])=[O:4].[OH-].[Na+].[CH2:15](Br)[CH:16]=[CH2:17]>CC(O)C.[Cl-].C([N+](CC)(CC)CC)C>[CH2:17]([C:7]1[CH:8]=[C:9]([CH3:12])[CH:10]=[CH:11][C:6]=1[S:3]([NH2:2])(=[O:5])=[O:4])[CH:16]=[CH2:15]

Participants

6

Reactant 3

HCID 7841Allyl bromideHCID 12543Benzenesulfonamide, N,4-dimethyl-HCID 14798Sodium Hydroxide

Product 1

HCID 67414600HCID 67414600, compound

Reagents, catalysts & solvents 2

HCID 5946Tetraethylammonium ChlorideCatalystHCID 3776IsopropanolSolvent

Procedure

N-methyl-4-methylbenzenesulfonamide (5.55 g, 0.05 mol) was dissolved in 2-propanol (75 ml). Tetraethyl ammonium chloride (0.1 g) and 50% sodium hydroxide (2.40 gm) were added to the solution. Allyl bromide (2.30 g, 0.03 mol) was added to the reaction mixture and the solution stirred for 1 hr. The solution was filtered to remove sodium bromide and the 2-propanol evaporated in vacuo. The crude product was diluted with ethyl acetate and washed with water (2×), dried over anhydrous magnesium sulfate and evaporated in vacuo to give N-methyl-N* allyl-4-methylbenzenesulfonamide. MS m/z 225. (M+ calcd for C11H15NO2S=225). H NMR (300 Mhz, CDCl3) d 2.44 (s, 3, CH3), 2.67 (s, 3, NCH3), 3.63 (m, 2, CH2 epoxypropyl), 5.21 (m, 2, CH2 epoxypropyl), 5.66-5.77 (m, 1, CH epoxypropyl), 7.33 (m, 2, aromatic), 7.67 (m, 2, aromatic).

Workup

  1. filtrationThe solution was filtered
  2. customto remove sodium bromide
  3. customthe 2-propanol evaporated in vacuo
  4. additionThe crude product was diluted with ethyl acetate
  5. washwashed with water (2×)
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-f0ac3ab1b457471a9ca2ddb60fb5cf9f
Source dataset
uspto-grants-2008_12
Patent number
US07462728B2

Reaction notes

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