Ethylamine → N-ethyl Nonylbenzene Sulfonamide

HRID 986541

반응식

HRID 986541 반응식
Cl[S:2]([OH:5])(=O)=[O:3].[C:6]1([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.S(Cl)(Cl)(=O)=O.[CH2:26]([NH2:28])[CH3:27].[OH-].[Na+]>O>[CH2:26]([NH:28][S:2]([C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=1[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])(=[O:5])=[O:3])[CH3:27]

참가 물질

7

반응물 5

HCID 6341EthylamineHCID 14126n-NonylbenzeneHCID 14798Sodium HydroxideHCID 24638Chlorosulfonic acid2회HCID 24648Sulfuryl chloride

생성물 1

HCID 14093327N-ethyl Nonylbenzene Sulfonamide수율 49%

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
25 °C

실험 절차

A 1 liter flask equipped as in Example 5 was charged with 1.72 moles (200.4 gms) of chlorosulfonic acid, and 0.49 moles (100 gms) of 1-phenylnonane was added to the vigorously stirred chlorosulfonic acid under N2 in 2 hours at 20° C. to 25° C. with cold water bath cooling. The mixture was stirred at 25° C. for 1/2 hour, then left to stand at room temperature under N2 overnight. The resulting crude sulfonyl chloride mixture was then added to a solution of 0.98 mole of ethylamine and 3.22 mole of NaOH in 275 ml of water in 0.5 hours at 55° C.±2° . The temperature was maintained at 55-°60° for 0.5 hour more with the pH above 10. Working up of the reaction mixture as in Example 5 gave 74.8 gms (49% yield) of amber liquid having a proton NMR spectra in CDCl3 consistent with the desired structure. The acidity of the product was 1.68 meq. per 100 gms. GC analysis showed that it was 98.8 percent sulfonamide (27.1 percent ortho, 5.7 percent meta and 67.2 percent para isomers).

후처리

  1. customA 1 liter flask equipped as in Example 5
  2. temperaturecooling
  3. waitleft
  4. waitto stand at room temperature under N2 overnight
  5. temperatureThe temperature was maintained at 55-°60° for 0.5 hour more with the pH above 10

출처 및 근거

ORD 기록
ord-677611aba703448c94120f4202a12685
출처 데이터셋
uspto-grants-1987_12
특허 번호
US04713489

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