Nitric Acid → HCID 18704790, compound

HRID 343397Notes

Reaction equation

HRID 343397 reaction equation
[N+:1]([O-:4])(O)=[O:2].[CH2:5]([C:9]1[CH:14]=[CH:13][C:12]([C:15]2[C:16]([S:21]([Cl:24])(=[O:23])=[O:22])=[CH:17][CH:18]=[CH:19][CH:20]=2)=[CH:11][CH:10]=1)[CH:6]([CH3:8])[CH3:7]>C(OC(=O)C)(=O)C>[CH2:5]([C:9]1[CH:10]=[CH:11][C:12]([C:15]2[C:16]([S:21]([Cl:24])(=[O:23])=[O:22])=[CH:17][CH:18]=[CH:19][CH:20]=2)=[CH:13][C:14]=1[N+:1]([O-:4])=[O:2])[CH:6]([CH3:8])[CH3:7]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 108286564'-Isobutyl-2-biphenylsulphonyl chloride

Product 1

HCID 18704790HCID 18704790, compound

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

Fuming nitric acid (0.8 ml) was added over 10 minutes to a stirred solution of 4'-isobutyl-2-biphenylsulphonyl chloride (3.09 g) in acetic anhydride (18 ml) at -20° C. The solution was kept at -20° C. for 1.5 hours and then allowed to warm to ambient temperature. The solution was stirred for 1.5 hours and then added to ice (300 g) with vigorous stirring. The mixture was stirred for 30 minutes and extracted with ether (3×100 ml) while still below 10° C. The ethereal solution was dried (MgSO4) and the solvent was removed by evaporation. The resulting oil was purified by flash chromatography, eluting with ethyl acetate/hexane (1:9 v/v), to give 4'-isobutyl-3'-nitro-2-biphenylsulphonyl chloride (2.01 g); 1H NMR (CDCl3): 0.95 (d,6H), 1.9-2.05 (m,1H), 2.9 (d,2H), 7.35-7.5 (m,2H), 7.6 (d,1H), 7.7 (d,1H), 7.8 (t,1H), 8.0 (s,1H), 8.25 (d,1H); mass spectrum (EI): 353(M+).

Workup

  1. stirringThe mixture was stirred for 30 minutes
  2. extractionextracted with ether (3×100 ml) while still below 10° C
  3. dry with materialThe ethereal solution was dried (MgSO4)
  4. customthe solvent was removed by evaporation
  5. customThe resulting oil was purified by flash chromatography
  6. washeluting with ethyl acetate/hexane (1:9 v/v)

Sources & evidence

ORD record
ord-1780b3c978684789bab313d02a56ca10
Source dataset
uspto-grants-1999_01
Patent number
US05861401

Reaction notes

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