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

HRID 1463777Notes

Reaction equation

HRID 1463777 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>[N+:11]([C:14]1[CH:15]=[C:16]([C:17]([NH:10][S:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)(=[O:9])=[O:8])=[O:18])[CH:20]=[CH:21][CH:22]=1)([O-:13])=[O:12]

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

Benzenesulphonamide (9.4 g, 60 mmol), 3-nitrobenzoic acid (10.0 g, 60 mmol), 4-dimethylaminopyridine (7.32 g, 60 mmol) and 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (11.48 g, 60 mmol) were stirred in anhydrous dichloromethane (400 ml) for 2 hours. The reaction mixture was extracted with 1M sodium hydroxide solution (300 ml), aqueous separated then re-acidified to pH=3 with 5M hydrochloric acid. 3-Nitro-(phenylsulphonylaminocarbonyl)benzene was isolated as a colourless solid (16.0 g, 87%), mp 186°-188° C.

Workup

  1. extractionThe reaction mixture was extracted with 1M sodium hydroxide solution (300 ml)
  2. customaqueous separated

Sources & evidence

ORD record
ord-a81437c66a5f4116b12bc7c9f740e0ee
Source dataset
uspto-grants-1994_04
Patent number
US05302591

Reaction notes

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