Butyl isocyanate → 2-(Chloromethyl)-N-(butylaminocarbonyl)benzenesulfonamide

HRID 279758

Reaktionsgleichung

Reaktionsgleichung von HRID 279758
[Cl:1][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[S:9]([NH2:12])(=[O:11])=[O:10].[CH2:13]([N:17]=[C:18]=[O:19])[CH2:14][CH2:15][CH3:16]>C1(C)C(C)=CC=CC=1.N12CCC(CC1)CN2>[Cl:1][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[S:9]([NH:12][C:18]([NH:17][CH2:13][CH2:14][CH2:15][CH3:16])=[O:19])(=[O:11])=[O:10]

Komponenten

5

Edukt 2

HCID 8110Butyl isocyanateHCID 133646272-(Chloromethyl)benzenesulfonamide

Produkt 1

HCID 136318872-(Chloromethyl)-N-(butylaminocarbonyl)benzenesulfonamideAusbeute 74,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 136165Diazabicyclo(2.2.2)octaneKatalysatorHCID 7237O-XyleneLösungsmittel

Versuchsvorschrift

A mixtue of 2-(chloromethyl)benzenesulfonamide (13.2 g, 64 mmol) and butyl isocyanate (7.0 g, 71 mmol) in xylene (80 ml) was contacted with diazabicyclo[2.2.2]-octane (0.25 g) and heated to reflux for 5.0 hrs. Volatiles were removed under vacuum and the residue was treated with 0.5N NaOH (200 ml) and extracted with ethyl acetate (75 ml). The aqueous layer was separated, chilled, acidified (pH 4) with hydrochloric acid, and extracted with ethyl acetate. The organic layer was washed with brine, dried (MgSO4), and evaporated to give 14.6 g of white solid. A sample was recrystallized from toluene to give m.p. 104°-106°.

Aufarbeitung

  1. temperatureheated
  2. temperatureto reflux for 5.0 hrs
  3. customVolatiles were removed under vacuum
  4. additionthe residue was treated with 0.5N NaOH (200 ml)
  5. extractionextracted with ethyl acetate (75 ml)
  6. customThe aqueous layer was separated
  7. temperaturechilled
  8. extractionextracted with ethyl acetate
  9. washThe organic layer was washed with brine
  10. dry with materialdried (MgSO4)
  11. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-201b00dd50774394a1d639d4e156cb20
Quelldatensatz
uspto-grants-1986_05
Patentnummer
US04586952

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