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

HRID 1577902Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1577902
[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]

Komponenten

5

Edukt 3

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

Produkt 1

HCID 205361454-(Butylsulfamoyl)phenyl 2-methylprop-2-enoateAusbeute 65,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

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 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.

Aufarbeitung

  1. temperaturewith cooling
  2. washwashed three times with water
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo in a warm 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

Quellen und Nachweise

ORD-Eintrag
ord-f8150e249ad545678f0effdd8b94cf1b
Quelldatensatz
uspto-grants-1981_09
Patentnummer
US04289865

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