Ethylamine → N-ethyl Nonylbenzene Sulfonamide

HRID 986541

反応式

HRID 986541 の反応式
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]

参加物

7

反応物 5

HCID 6341EthylamineHCID 14126n-NonylbenzeneHCID 14798Sodium HydroxideHCID 24638Chlorosulfonic acid2 回HCID 24648Sulfuryl chloride

生成物 1

HCID 14093327N-ethyl Nonylbenzene Sulfonamide収率 49%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
25 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-677611aba703448c94120f4202a12685
出典データセット
uspto-grants-1987_12
特許番号
US04713489

関連ノート

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