Chloroform → 4-Chloro-N-methyl-3-nitro-N-octadecylbenzene-1-sulfonamide
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
5
Conditions
- Temperature
- 0 °C
Procedure
300 ml of chloroform was added to 100 g of 4-chloro-3-nitrobenzenesulfonyl chloride. The solution was then cooled to a temperature of 0° C. A chloroform solution of 84.3 g of methyloctadecylamine was added dropwise to the solution. 39.5 g of triethylamine was then added dropwise to the solution while the temperature thereof was kept at 0° to 10° C. The solution was stirred at room temperature for 1 hour. Chloroform was removed from the solution under reduced pressure. 500 ml of methanol was added to the residue. The reaction mixture was heated to complete dissolution. The solution was cooled., The resulting crystals were filtered off and dried. (Yield: 109 g (71%); m.p.: 86°-87° C.)
Workup
- customthereof was kept at 0° to 10° C
- customChloroform was removed from the solution under reduced pressure
- addition500 ml of methanol was added to the residue
- temperatureThe reaction mixture was heated
- dissolutiondissolution
- temperatureThe solution was cooled
- filtration, The resulting crystals were filtered off
- customdried
Sources & evidence
- ORD record
- ord-6e993effdf964c4fad692a00f31a6c69
- Source dataset
- uspto-grants-1991_09
- Patent number
- USH0000963
Reaction notes
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