Hydrochloric Acid → 4-Nitro-2-(trifluoromethyl)benzene-1-sulfonyl chloride

HRID 1841943Notes

Reaction equation

HRID 1841943 reaction equation
N([O-])=O.[Na+].[N+:5]([C:8]1[CH:13]=[CH:12][C:11](N)=[C:10]([C:15]([F:18])([F:17])[F:16])[CH:9]=1)([O-:7])=[O:6].[S:19](=[O:21])=[O:20].O.[ClH:23]>C(O)(=O)C.[Cu](Cl)Cl>[N+:5]([C:8]1[CH:13]=[CH:12][C:11]([S:19]([Cl:23])(=[O:21])=[O:20])=[C:10]([C:15]([F:18])([F:17])[F:16])[CH:9]=1)([O-:7])=[O:6]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 962WaterHCID 1119Sulfur DioxideHCID 671284-Nitro-alpha,alpha,alpha-trifluoro-o-toluidineHCID 23668193Sodium Nitrite

Product 1

HCID 108034044-Nitro-2-(trifluoromethyl)benzene-1-sulfonyl chlorideYield 71%

Reagents, catalysts & solvents 2

HCID 24014Cupric ChlorideCatalystHCID 176Acetic AcidSolvent2×

Procedure

Sodium nitrite (1.8 g, 26 mmol) was added portion wise to a stirred solution of 4-nitro-2-trifluoromethyl-phenylamine (5.0 g, 24 mmol) in acetic acid (37 ml) and HCl (concentrated, 7.5 ml) while maintaining the temperature below 15° C. This solution was then added drop wise to a stirred solution of saturated sulfur dioxide, copper (II) chloride (0.6 g, 4.5 mmol) and water (7.5 ml) in acetic acid (24 ml) at 5° C. The reaction mixture was allowed to warm to room temperature and poured over ice water and stirred for a further 15 minutes. The resulting precipitate was collected by filtration, washed with water and dried overnight in a vacuum oven to give the title compound (3.5 g, 71% yield) as a yellow solid which was used without further purification.

Workup

  1. temperaturewhile maintaining the temperature below 15° C
  2. filtrationThe resulting precipitate was collected by filtration
  3. washwashed with water
  4. customdried overnight in a vacuum oven

Sources & evidence

ORD record
ord-c66378d7c6264624917f5d8466e81ecc
Source dataset
uspto-grants-2015_02
Patent number
US08946197B2

Reaction notes

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