Hydrochloric Acid → 2-Chloro-4-nitrobenzene-1-sulfonyl chloride

HRID 1868415Notes

Reaction equation

HRID 1868415 reaction equation
[ClH:1].[Cl:2][C:3]1[CH:9]=[CH:8][C:6](N)=[C:5]([N+:10]([O-:12])=[O:11])[CH:4]=1.N([O-])=O.[Na+].[S:17](=[O:19])=[O:18]>O.C(O)(=O)C.[Cu]Cl>[Cl:2][C:3]1[CH:4]=[C:5]([N+:10]([O-:12])=[O:11])[CH:6]=[CH:8][C:9]=1[S:17]([Cl:1])(=[O:19])=[O:18]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 1119Sulfur DioxideHCID 69794-Chloro-2-nitroanilineHCID 23668193Sodium Nitrite

Product 1

HCID 2845712-Chloro-4-nitrobenzene-1-sulfonyl chlorideYield 69%

Reagents, catalysts & solvents 3

HCID 62652Cuprous chlorideCatalystHCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

In a beaker charged with 15 mL of concentrated hydrochloric acid was added 1 g (5.8 mmol) of 4-chloro-2-nitroaniline. The mixture stirred for 30 minutes at room temperature. The mixture was then chilled (−5° C.) and 400 mg (5.8 mmol) of sodium nitrite in 10 mL of water was added in several portions while maintaining the temperature between −5° C. and 10° C. After 30 minutes, the diazonium salt mixture was added in several portions to a chilled (ice-water bath) solution of 115 mg (1.16 mmol) of copper (I) chloride in 25 mL of acetic acid saturated with sulfur dioxide gas. The mixture was allowed to warm to room temperature. After 40 minutes, the mix was poured on to ice and stirred until the ice was melted. The bright yellow solid was collected by filtration, washed with several portions of water, and dried to afford 1.03 g (69%) of 2-chloro-4-nitrobenzenesulfonyl chloride.

Workup

  1. additionwas added in several portions
  2. temperaturewhile maintaining the temperature between −5° C. and 10° C
  3. waitAfter 30 minutes
  4. temperatureto warm to room temperature
  5. waitAfter 40 minutes
  6. additionthe mix was poured on to ice
  7. filtrationThe bright yellow solid was collected by filtration
  8. washwashed with several portions of water
  9. customdried

Sources & evidence

ORD record
ord-70119d55d17e4d828275a37b26d736ba
Source dataset
uspto-grants-2009_12
Patent number
US07635711B2

Reaction notes

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