Benzoic Acid → N-(3-nitrophenyl)sulfonylbenzamide

HRID 2379322Notes

Reaction equation

HRID 2379322 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([S:10]([NH2:13])(=[O:12])=[O:11])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[C:14](O)(=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.Cl.CN(C)CCCN=C=NCC>CN(C)C1C=CN=CC=1.ClCCl>[C:15]1([C:14]([NH:13][S:10]([C:6]2[CH:7]=[CH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)(=[O:11])=[O:12])=[O:21])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 3

HCID 243Benzoic AcidHCID 67138Benzenesulfonamide, 3-nitro-HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 2947178N-(3-nitrophenyl)sulfonylbenzamideYield 86%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared in the some way as that described in Example 11, Step 1, using 3-nitrobenzenesulphonamide (10.1 g, 50 mml), benzoic acid (6.1 g, 50 mmol), 4-dimethylaminopyridine (6.1 g, 50 mmol), 1-[3-(dimethylamino)propyl]-3-ethyl carbodiimide hydrochloride (9.59 g, 50 mmol) and anhydrous dichloromethane (400ml). The title compound (13.1 g, 86%) was afforded as a colourless solid. mp 181°-183° C. 1H NMR (360 MHz, D6 -DMSO) δ 7.49 (2H, m), 7.61-7.66 (1H, m), 7.86-7.89 (2H, m), 7.96 (1H, dd, J=8.0 and 8.0 Hz), 8.43 (1H, m), 8.56 (1H, m), 8.71 (1H, m).

Workup

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

Sources & evidence

ORD record
ord-7d6ba7906ea048589c15fb3262caab87
Source dataset
uspto-grants-1994_11
Patent number
US05360802

Reaction notes

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