3-Nitrobenzoic acid → 1-(1,1-Dimethylethylsulphonylaminocarbonyl)-3-nitrobenzene

HRID 2379349노트

반응식

HRID 2379349 반응식
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][CH:12]=1)[C:7]([OH:9])=O)([O-:3])=[O:2].[CH3:13][C:14]([S:17]([NH2:20])(=[O:19])=[O:18])([CH3:16])[CH3:15].Cl.CN(C)CCCN=C=NCC>CN(C)C1C=CN=CC=1.ClCCl>[CH3:13][C:14]([CH3:16])([S:17]([NH:20][C:7]([C:6]1[CH:10]=[CH:11][CH:12]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1)=[O:9])(=[O:19])=[O:18])[CH3:15]

참가 물질

6

반응물 3

HCID 84973-Nitrobenzoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2757335tert-Butylsulfonamide

생성물 1

HCID 189577801-(1,1-Dimethylethylsulphonylaminocarbonyl)-3-nitrobenzene수율 85%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매

실험 절차

To a mixture of 3-nitrobenzoic acid (0.37 g, 2.2 mmol), 1,1-dimethylethylsulphonamide (0.3 g, 2.2 mmol) and 4-dimethylaminopyridine (0.27 g, 2.2 mmol) in anhydrous dichloromethane (20 ml), under an atmosphere of nitrogen, was added. 1-[3-(dimethylamino)propyl]-3-ethyl carbodiimide hydrochloride (0.42 g, 2.2 mmol). The mixture was stirred at ambient temperature for 22 h. The mixture was extracted with 1M NaOH (50 ml) and the separated aqueous phase acidified using 5M HCl. This was extracted with dichloromethane (5×20 ml), then the combined organic extracts were dried (Na2SO4) and evaporated to dryness. The residue was chromatographed on silica gel using 1% methanol in dichloromethane as the eluant. The title compound (0.53 g, 85%) was isolated as a colourless solid. mp 220° C. 1H NMR (360 MHz, D6-DMSO) δ 1.27 (9H, s), 6.59 (1H, brs), 7.65 (1H, t, J=7.9 Hz), 8.24-8.30 (1H, m), 8.34-8.38 (1H, m), 8.68-8.72 (1H, m).

후처리

  1. additionunder an atmosphere of nitrogen, was added
  2. extractionThe mixture was extracted with 1M NaOH (50 ml)
  3. extractionThis was extracted with dichloromethane (5×20 ml)
  4. dry with materialthe combined organic extracts were dried (Na2SO4)
  5. customevaporated to dryness
  6. customThe residue was chromatographed on silica gel using 1% methanol in dichloromethane as the eluant

출처 및 근거

ORD 기록
ord-6418b30647d4438193b56c2333ae2ed4
출처 데이터셋
uspto-grants-1994_11
특허 번호
US05360802

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