Nitric Acid → 4'-Isobutyl-3'-nitro-2-biphenylsulphonyl chloride

HRID 2287409노트

반응식

HRID 2287409 반응식
[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]

참가 물질

5

반응물 3

HCID 944Nitric AcidHCID 3283Diethyl EtherHCID 108286564'-Isobutyl-2-biphenylsulphonyl chloride

생성물 1

HCID 187047904'-Isobutyl-3'-nitro-2-biphenylsulphonyl chloride

시약·촉매·용매 1

HCID 7918Acetic Anhydride용매

실험 절차

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+).

후처리

  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)

출처 및 근거

ORD 기록
ord-af5669d138054d0c83b92c3c5ecea140
출처 데이터셋
uspto-grants-2000_07
특허 번호
US06083951

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