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

HRID 2379349ノート

反応式

HRID 2379349 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

HCID 189577801-(1,1-Dimethylethylsulphonylaminocarbonyl)-3-nitrobenzene収率 85%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-6418b30647d4438193b56c2333ae2ed4
出典データセット
uspto-grants-1994_11
特許番号
US05360802

反応ノート

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