Water → HCID 14952978, compound

HRID 893347Notes

Reaction equation

HRID 893347 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][C:13]=2[N+:20]([O-:22])=[O:21])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[OH-].[Na+].[Cl:25][C:26]1[CH:33]=[CH:32][C:29]([CH2:30]Cl)=[CH:28][CH:27]=1.O>CCOCC>[Cl:25][C:26]1[CH:33]=[CH:32][C:29]([CH2:30][N:11]([S:8]([C:5]2[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][CH:4]=2)(=[O:9])=[O:10])[C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][C:13]=2[N+:20]([O-:22])=[O:21])=[CH:28][CH:27]=1

Participants

6

Reactant 4

HCID 962WaterHCID 77231-Chloro-4-(chloromethyl)benzene2×HCID 14798Sodium Hydroxide2×HCID 225676N-(4-Methoxy-2-nitrophenyl)-4-methylbenzenesulfonamide

Product 1

HCID 14952978HCID 14952978, compoundYield 120.9%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

72.8 g of 2-(4-methylbenzenesulfonylamino)-5-methoxynitrobenzene, prepared in A), are added to 56.5 ml of 4N sodium hydroxide solution and 29.2 g of 4-chlorobenzyl chloride. The mixture is refluxed for 4 hours, a further 43.7 g of 4-chlorobenzyl chloride are then added and the resulting mixture is refluxed for another 45 minutes. After cooling, 12.2 ml of 35% sodium hydroxide solution are added to the reaction mixture, the latter is refluxed for three hours 45 minutes and then cooled and water and ether are added. The insoluble material is filtered off and washed with water and ether to give 98 g of N-(4-chlorobenzyl)-N-(4-methylbenzenesulfonyl)-2-nitro-4-methoxyaniline in the form of crystals melting at 124° C. Evaporation of the ether phase yields an additional 10 g of crystals melting at 124° C.

Workup

  1. temperatureThe mixture is refluxed for 4 hours
  2. temperaturethe resulting mixture is refluxed for another 45 minutes
  3. temperatureAfter cooling
  4. temperaturethe latter is refluxed for three hours 45 minutes
  5. temperaturecooled
  6. filtrationThe insoluble material is filtered off
  7. washwashed with water and ether

Sources & evidence

ORD record
ord-ef4694e879ba4b00885cca1eb546e1ce
Source dataset
uspto-grants-1992_06
Patent number
US05124336

Reaction notes

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