Triethylamine → 4-(Butylsulfamoyl)phenyl 2-methylprop-2-enoate

HRID 1156418Notes

Reaction equation

HRID 1156418 reaction equation
[C:1](Cl)(=[O:5])[C:2]([CH3:4])=[CH2:3].[CH2:7]([NH:11][S:12]([C:15]1[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=1)(=[O:14])=[O:13])[CH2:8][CH2:9][CH3:10].C(N(CC)CC)C>C(Cl)Cl>[CH2:7]([NH:11][S:12]([C:15]1[CH:16]=[CH:17][C:18]([O:21][C:1](=[O:5])[C:2]([CH3:4])=[CH2:3])=[CH:19][CH:20]=1)(=[O:14])=[O:13])[CH2:8][CH2:9][CH3:10]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 13528Methacryloyl chlorideHCID 11736345N-Butyl-4-hydroxybenzenesulfonamide

Product 1

HCID 205361454-(Butylsulfamoyl)phenyl 2-methylprop-2-enoateYield 65.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 20.91 g (0.20 mol) of methacryloyl chloride in 80 ml of methylene chloride was added to a solution of 45.86 g (0.20 mol) of N-butyl-4-hydroxybenzenesulfonamide, 20.24 g (0.20 mol) of triethylamine and 320 ml of methylene chloride and cooled to 0° C. over a period of approximately 20 minutes. The mixture was then stirred for another 1.5 hours with cooling, washed three times with water, dried over magnesium sulfate and concentrated in vacuo in a warm water bath. The resultant oil (Note 1) was cooled and crystallized to an oily solid. Removal of residual solvent with high vacuum caused this material to completely solidify. This solid was recrystallized from 600 ml of cyclohexane with filtering. Collection of the white solid and drying at room temperature in vacuo gave 38.9 g of N-butyl-4-methacryloyloxybenzenesulfonamide; m.p.=59° to 60° C.

Workup

  1. temperaturewith cooling
  2. washwashed three times with water
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo in a warm water bath
  5. temperatureThe resultant oil (Note 1) was cooled
  6. customcrystallized to an oily solid
  7. customRemoval of residual solvent with high vacuum
  8. customThis solid was recrystallized from 600 ml of cyclohexane
  9. filtrationwith filtering
  10. customCollection of the white solid
  11. customdrying at room temperature in vacuo

Sources & evidence

ORD record
ord-593e6f0fef2f43f194cefeff301ba1ef
Source dataset
uspto-grants-1982_06
Patent number
US04335254

Reaction notes

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