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

HRID 2379349Notes

Reaction equation

HRID 2379349 reaction equation
[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]

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-6418b30647d4438193b56c2333ae2ed4
Source dataset
uspto-grants-1994_11
Patent number
US05360802

Reaction notes

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