Hydrochloric Acid → 4-methoxy-2-nitro-N-(4-chlorophenyl)benzenesulfonamide

HRID 477875Notes

Reaction equation

HRID 477875 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.[CH3:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([S:17](Cl)(=[O:19])=[O:18])=[C:13]([N+:21]([O-:23])=[O:22])[CH:12]=1.[OH-].[Na+].Cl>>[CH3:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([S:17]([NH:6][C:5]2[CH:7]=[CH:8][C:2]([Cl:1])=[CH:3][CH:4]=2)(=[O:18])=[O:19])=[C:13]([N+:21]([O-:23])=[O:22])[CH:12]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 78124-ChloroanilineHCID 14798Sodium HydroxideHCID 874524-Methoxy-2-nitrobenzenesulphonyl chloride

Product 1

HCID 9546834-methoxy-2-nitro-N-(4-chlorophenyl)benzenesulfonamideYield 95.8%

Procedure

To a mixture of 4-chloroaniline (14.51 g) and 4-methoxy-2-nitrobenzenesulfonyl chloride (28.54 g) was added dropwise aqueous sodium hydroxide solution (0.7 N, 162 ml) over a period of 30 minutes at 70° C. After addition, the mixture was stirred for 30 minutes at the same temperature. The colled mixture was diluted with aqueous IN-hydrochloric acid. The separated oil was extracted with ethyl acetate. The extract was dried over magnesium sulfate and concentrated under reduced pressure. The yellow solid was triturated with n-hexame and collected by filtration to yield 4-methoxy-2-nitro-N-(4-chlorophenyl) benzenesulfonamide (37,23 g).

Workup

  1. additionAfter addition
  2. extractionThe separated oil was extracted with ethyl acetate
  3. dry with materialThe extract was dried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe yellow solid was triturated with n-hexame and
  6. filtrationcollected by filtration

Sources & evidence

ORD record
ord-b4361b7ec8dd41ed89a205d8f818c782
Source dataset
uspto-grants-1989_12
Patent number
US04889851

Reaction notes

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