Chloroform → 4-Chloro-N-methyl-3-nitro-N-octadecylbenzene-1-sulfonamide

HRID 2165037Notes

Reaction equation

C(Cl)(Cl)Cl.[Cl:5][C:6]1[CH:11]=[CH:10][C:9]([S:12](Cl)(=[O:14])=[O:13])=[CH:8][C:7]=1[N+:16]([O-:18])=[O:17].[CH3:19][NH: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][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38]>C(N(CC)CC)C>[Cl:5][C:6]1[CH:11]=[CH:10][C:9]([S:12]([N:20]([CH3:19])[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][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38])(=[O:14])=[O:13])=[CH:8][C:7]=1[N+:16]([O-:18])=[O:17]

Participants

Conditions

Temperature: 0 °C

Procedure

300 m(of chloroform was added to 100 g of 4-chloro-3-nitrobenzenesulfonyl chloride and the mixture was cooled to 0° C. Then, a chloroform solution containing 84.3 g of methyloctadecylamine was added dropwise to the mixture. After 39.5 g of triethylamine was added dropwise thereto while the temperature was kept at 0° to 10° C.., the mixture was stirred for 1 hour at room temperature. The chloroform was distilled off under reduced pressure, then 500 ml of methanol was added to the residue, and it was heated to dissolve the residue. The mixture was cooled to precipitate crystals and the crystals were filtered and dried.

Workup

additionwas added dropwise to the mixture
customwas kept at 0° to 10° C.
distillationThe chloroform was distilled off under reduced pressure
addition500 ml of methanol was added to the residue, and it
temperaturewas heated
dissolutionto dissolve the residue
temperatureThe mixture was cooled
customto precipitate crystals
filtrationthe crystals were filtered
customdried

Sources & evidence

ORD record: ord-464be7488b754ddda807d8eaf0ed5941
Source dataset: uspto-grants-1990_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04939066

Reaction notes

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