Hydrochloric Acid → N-Benzyl-2-acetyl-6-chloro-3-nitrobenzenesulfonamide

HRID 2301495Notes

Reaction equation

[C:1]([C:4]1[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][CH:7]=[C:6]([Cl:13])[C:5]=1[S:14]([NH2:17])(=[O:16])=[O:15])(=[O:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[CH2:24](Br)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.Cl>CN(C)C=O>[CH2:24]([NH:17][S:14]([C:5]1[C:6]([Cl:13])=[CH:7][CH:8]=[C:9]([N+:10]([O-:12])=[O:11])[C:4]=1[C:1](=[O:3])[CH3:2])(=[O:15])=[O:16])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

Conditions

Temperature: 75 °C

Procedure

A mixture of 2-acetyl-6-chloro-3-nitrobenzenesulfonamide (500 mg, 1.69 mmol), potassium carbonate (469 mg, 3.39 mmnol) and benzyl bromide (0.24 mL, 2.0 mmol) in 20 mL of N,N-dimethylformamide was heated to 75° C for 24 hours. The mixture was acidified with 1 N aq. HCl, then extracted with ethyl acetate. The solvent was concentrated to give the crude material. Column chromatography on silica gel, eluting with ethyl acetate/hexane/acetic acid (50/49/1, v/v/v), gave the desired product (274 mg, 42%). EI-MS (m/z) 383.3, 385.3 (M−).

Workup

extractionextracted with ethyl acetate
concentrationThe solvent was concentrated
customto give the crude material
washColumn chromatography on silica gel, eluting with ethyl acetate/hexane/acetic acid (50/49/1, v/v/v)

Sources & evidence

ORD record: ord-4d1b0cbe9e3e4143a34be89120a907aa
Source dataset: uspto-grants-2002_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06500863B1

Reaction notes

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