Benzenesulfonamide → 3-nitro-N-(phenylsulfonyl)Benzamide

HRID 2379325Notes

Reaction equation

HRID 2379325 reaction equation
[C:1]1([S:7]([NH2:10])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N+:11]([C:14]1[CH:15]=[C:16]([CH:20]=[CH:21][CH:22]=1)[C:17](O)=[O:18])([O-:13])=[O:12].Cl.CN(C)CCCN=C=NCC>CN(C)C1C=CN=CC=1.ClCCl>[C:1]1([S:7]([NH:10][C:17]([C:16]2[CH:20]=[CH:21][CH:22]=[C:14]([N+:11]([O-:13])=[O:12])[CH:15]=2)=[O:18])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 7370BenzenesulfonamideHCID 84973-Nitrobenzoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 9757333-nitro-N-(phenylsulfonyl)Benzamide

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 benzenesulphonamide (4.7 g, 30 mmol), 3-nitrobenzoic acid (5 g,30 mmol), 4-dimethylamino pyridine (3.66 g, 30 mmol), 1-[3-(dimethylamino)propyl]-3-ethyl carbodiimide hydrochloride (5.74 g, 30 mmol), and anhydrous dichloromethane (200 ml). The compound (8.05 g, 88%) was afforded as a colourless solid. mp 188°-190° C. 1H NMR (360 MHz, D6 -DMSO) δ 7.65 (2H, m), 7.72 (1H, m), 7.79 (1H,dd, J=8.0 and 8.0 Hz), 8.02 (2H, m), 8.28 (1H, dd, J=8.0 and 1.5 Hz), 8.45 (1H, dd, J: 8.0 and 1.5 Hz), 8.72 (1H, m).

Sources & evidence

ORD record
ord-b1faac6485d14b2e92f0f8b3f430847a
Source dataset
uspto-grants-1994_11
Patent number
US05360802

Reaction notes

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