Triethylamine → N-(4-EThenylphenyl)methanesulfonamide

HRID 461752

반응식

HRID 461752 반응식
[CH:1]([C:3]1[CH:9]=[CH:8][C:6]([NH2:7])=[CH:5][CH:4]=1)=[CH2:2].C(N(CC)CC)C.[CH3:17][S:18](Cl)(=[O:20])=[O:19]>C(OCC)C>[CH:1]([C:3]1[CH:9]=[CH:8][C:6]([NH:7][S:18]([CH3:17])(=[O:20])=[O:19])=[CH:5][CH:4]=1)=[CH2:2]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 737004-Aminostyrene

생성물 1

HCID 54237795N-(4-EThenylphenyl)methanesulfonamide수율 70%

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

실험 절차

To a solution of 500 g (4.2 moles) of 4-vinylaniline and 460 g (4.2 moles) of triethylamine in 1000 cc of anhydrous diethyl ether under a nitrogen atmosphere was added dropwise 478 g (4.2 moles) of methanesulfonyl chloride. The temperature of the reaction vessel was kept below 5° C by an ice bath during the course of the reaction. When addition was complete (40 min.), the mixture was stirred for an additional 2 hours and the contents of the flask then brought to room temperature. The mixture was filtered and extracted with 500 cc of 1.0 M HCl solution. The etheral portion was separated, dried and the ether removed on a rotary evaporator. The resulting oily solid was extracted with 500 cc of ethanol and recrystallized from ethane/water and then from toluene. 70-75% yield after recrystallization. M.P. = 97° C.

후처리

  1. customThe temperature of the reaction vessel was kept below 5° C by an ice bath during the course of the reaction
  2. additionWhen addition
  3. custom(40 min.)
  4. customthen brought to room temperature
  5. filtrationThe mixture was filtered
  6. extractionextracted with 500 cc of 1.0 M HCl solution
  7. customThe etheral portion was separated
  8. customdried
  9. customthe ether removed on a rotary evaporator
  10. extractionThe resulting oily solid was extracted with 500 cc of ethanol
  11. customrecrystallized from ethane/water
  12. custom70-75% yield after recrystallization

출처 및 근거

ORD 기록
ord-05b11a8203004527a63ef1b6f0f5359a
출처 데이터셋
uspto-grants-1977_12
특허 번호
US04064168

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