Ethylamine → N-ethyl Nonylbenzene Sulfonamide

HRID 986541

Reaction equation

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]

Participants

Conditions

Temperature: 25 °C

Procedure

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).

Workup

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

Sources & evidence

ORD record: ord-677611aba703448c94120f4202a12685
Source dataset: uspto-grants-1987_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04713489

Linked notes

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