3-Nitrobenzoic acid → 1-(Ethylsulphonylaminocarbonyl)-3-nitrobenzene

HRID 2379338Notes

Reaction equation

HRID 2379338 reaction equation
[CH2:1]([S:3]([NH2:6])(=[O:5])=[O:4])[CH3:2].[N+:7]([C:10]1[CH:11]=[C:12]([CH:16]=[CH:17][CH:18]=1)[C:13](O)=[O:14])([O-:9])=[O:8].Cl.CN(C)CCCN=C=NCC>CN(C)C1C=CN=CC=1.ClCCl>[CH2:1]([S:3]([NH:6][C:13]([C:12]1[CH:16]=[CH:17][CH:18]=[C:10]([N+:7]([O-:9])=[O:8])[CH:11]=1)=[O:14])(=[O:5])=[O:4])[CH3:2]

Participants

6

Reactant 3

HCID 84973-Nitrobenzoic acidHCID 73702EthanesulfonamideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 189577921-(Ethylsulphonylaminocarbonyl)-3-nitrobenzeneYield 84.5%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared in the same way as that described in Example 11, Step 1, using ethyl sulphonamide (3 g, 27.5 mmol), 3-nitrobenzoic acid (4.6 g, 27.5 mmol), 4-dimethylaminopyridine (3.36 g, 27.5 mmol), 1-[3-(dimethylamino)propyl]-3-ethyl carbodiimide hydrochloride (5.28 g, 27.5 mmol) and anhydrous dichloromethane (200 ml). The title compound (6 g, 84%) was afforded as a colourless solid. mp 178°-181° C. 1H NMR (360 MHz, D6 -DMSO) δ 1.28 (3H, t, J=7.4 Hz), 3.54 (2H, q, J=7.4 Hz), 7.83 (1H, dd, J=8.0 and 8.0 Hz), 8.33-8.38 (1H, m), 8.47-8.50 (1H, m), 8.75-8.90 (1H, m), 12.40 (1H, brs).

Workup

  1. customThe title compound was prepared in the same way as

Sources & evidence

ORD record
ord-b4caf17056f04c9b9fd9763b80982c90
Source dataset
uspto-grants-1994_11
Patent number
US05360802

Reaction notes

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