Water → 4-chloro-N-hexadecyl-N-methyl-3-nitrobenzenesulfonamide
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])(=[O:10])=[O:9])=[CH:4][C:3]=1[N+:28]([O-:30])=[O:29].[C:31](=O)([O-])[O-].[K+].[K+].COS(=O)(=O)OC.O>CC(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]([CH3:31])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])(=[O:9])=[O:10])=[CH:4][C:3]=1[N+:28]([O-:30])=[O:29]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
In 640 ml of acetone was dissolved 170 g of 4-chloro-3-nitro-N-hexadecylbenzenesulfonamide prepared in the above step and after adding thereto 79 g of potassium carbonate, 6 ml of polyethylene glycol (average molecular weight: 400), and 71 g of dimethylsulfuric acid, the mixture was refluxed for 5 hours. To the reaction mixture thus obtained was added 240 ml of acetone and after adding dropwise 870 ml or water to the mixture at 40° C., the resultant mixture was cooled to room temperature, whereby crystals deposited. The crystals were recovered by filtration, washed with water and then methanol, and dried to provide 169 g of the above-described compound with a yield of 97%. The melting point thereof was 74° C. to 75° C.
Workup
- customprepared in the above step
- additionafter adding
- customTo the reaction mixture thus obtained
- filtrationThe crystals were recovered by filtration
- washwashed with water
- dry with materialmethanol, and dried
Sources & evidence
- ORD record
- ord-c27552ff90c946cea5fa512c213f9193
- Source dataset
- uspto-grants-1991_12
- Patent number
- US05071994
Reaction notes
Loading…