Sodium Iodide → N-1-butanesulfonyl-3-(2,4-dichlorobenzylamino)-4-nitrobenzamide

HRID 276080Notes

Reaction equation

[CH2:1]([S:5]([NH:8][C:9](=[O:20])[C:10]1[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[C:12]([NH2:19])[CH:11]=1)(=[O:7])=[O:6])[CH2:2][CH2:3][CH3:4].[I-].[Na+].C(=O)([O-])[O-].[K+].[K+].[Cl:29][C:30]1[CH:37]=[C:36]([Cl:38])[CH:35]=[CH:34][C:31]=1[CH2:32]Cl>C(OCC)(=O)C.CO>[CH2:1]([S:5]([NH:8][C:9](=[O:20])[C:10]1[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[C:12]([NH:19][CH2:32][C:31]2[CH:34]=[CH:35][C:36]([Cl:38])=[CH:37][C:30]=2[Cl:29])[CH:11]=1)(=[O:7])=[O:6])[CH2:2][CH2:3][CH3:4]

Participants

Conditions

Temperature: 60 °C

Procedure

A solution containing 1.10 g of N-1-butanesulfonyl-3-amino-4-nitrobenzamide, 0.273 g of sodium iodide, 1.54 g of potassium carbonate, 2.17 g of 2,4-dichlorobenzyl chloride and 10 ml of methanol was stirred at 60° C. for 24 hours. Further, 2.00 g of 2,4-dichlorobenzyl chloride were added thereto, and the mixture was heated at 60° C. for 36 hours. To the reaction solution were added ethyl acetate and a saturated aqueous solution of sodium hydrogencarbonate, and N-1-butanesulfonyl-3-(2,4-dichlorobenzylamino)-4-nitrobenzamide was extracted in the aqueous layer. The organic layer was concentrated to give 0.885 g of N-1-butanesulfonyl-3-(2,4-dichlorobenzylamino)-4-nitrobenzamide.

Workup

temperaturethe mixture was heated at 60° C. for 36 hours
extractiona saturated aqueous solution of sodium hydrogencarbonate, and N-1-butanesulfonyl-3-(2,4-dichlorobenzylamino)-4-nitrobenzamide was extracted in the aqueous layer
concentrationThe organic layer was concentrated

Sources & evidence

ORD record: ord-898d436535db481595ac9e4346de175f
Source dataset: uspto-grants-2002_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06352985B1

Reaction notes

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