Benzenesulfonyl chloride, 4-chloro-3-nitro- → 4-Chloro-N-methyl-3-nitro-N-octadecylbenzene-1-sulfonamide

HRID 728529Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].[CH3:15][NH:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34].C(N(CC)CC)C>C(Cl)(Cl)Cl>[CH3:15][N:16]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])[S:8]([C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[C:3]([N+:12]([O-:14])=[O:13])[CH:4]=1)(=[O:10])=[O:9]

Participants

Conditions

Temperature: 0 °C

Procedure

In 300 ml of chloroform, 100 g of 4-chloro-3-nitrobenzenesulfonyl chloride was dissolved, and cooled to 0° C. Thereto, a solution of 84.3 g of methyloctadecylamine in chloroform was added dropwise. Then, 39.5 g of triethylamine was added dropwise as the reaction system was kept at a temperature from 0° C. to 10° C. After the conclusion of the addition, the reaction was run for 1 hour. Then, the solvent was distilled away, and the residue was dissolved in 500 ml of methanol under heating. The solution was allowed to stand for a while in order to cool. Thereupon, crystals separated out, and they were filtered off. Yield: 109 g, Percent yield: 71.2%, Melting point: 86°-87° C.

Workup

customwas kept at a temperature from 0° C. to 10° C
additionAfter the conclusion of the addition
distillationThen, the solvent was distilled away
dissolutionthe residue was dissolved in 500 ml of methanol
temperatureunder heating
temperatureto cool
customThereupon, crystals separated out
filtrationthey were filtered off

Sources & evidence

ORD record: ord-92043e01933842cba172fbe0064fe547
Source dataset: uspto-grants-1991_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05049477

Reaction notes

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