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

HRID 279758

반응식

HRID 279758 반응식
[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]

참가 물질

5

반응물 2

HCID 8110Butyl isocyanateHCID 133646272-(Chloromethyl)benzenesulfonamide

생성물 1

HCID 136318872-(Chloromethyl)-N-(butylaminocarbonyl)benzenesulfonamide수율 74.8%

시약·촉매·용매 2

HCID 136165Diazabicyclo(2.2.2)octane촉매HCID 7237O-Xylene용매

실험 절차

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°.

후처리

  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

출처 및 근거

ORD 기록
ord-201b00dd50774394a1d639d4e156cb20
출처 데이터셋
uspto-grants-1986_05
특허 번호
US04586952

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