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

HRID 4145

Reaktionsgleichung

Reaktionsgleichung von HRID 4145
[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 mixture 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-96b36f56b2bf4e2fa59c2f023ae48e35
Quelldatensatz
uspto-grants-1988_02
Patentnummer
US04723990

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