Nitric Acid → HCID 18704790, compound

HRID 2287409Notes

Reaction equation

HRID 2287409 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].CCOCC>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

5

Reactant 3

HCID 944Nitric AcidHCID 3283Diethyl EtherHCID 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 sextracted with ether 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. extractionextracted with ether (3×100 ml) while still below 10° C
  2. dry with materialThe ethereal solution was dried (MgSO4)
  3. customthe solvent was removed by evaporation
  4. customThe resulting oil was purified by flash chromatography
  5. washeluting with ethyl acetate/hexane (1:9 v/v)

Sources & evidence

ORD record
ord-af5669d138054d0c83b92c3c5ecea140
Source dataset
uspto-grants-2000_07
Patent number
US06083951

Reaction notes

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