N-(3-Bromopropyl)-2-nitrobenzamide → HCID 54510921, compound

HRID 1608832Notes

Reaction equation

Br[CH2:2][CH2:3][CH2:4][NH:5][C:6](=[O:16])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[N+:13]([O-:15])=[O:14].[NH:17]1[CH:21]=[N:20][N:19]=[N:18]1>CN(C)C=O>[NH:20]1[CH:21]=[N:17][NH:18][N:19]1[CH2:2][CH2:3][CH2:4][NH:5][C:6](=[O:16])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[N+:13]([O-:15])=[O:14]

Participants

Conditions

Temperature: 50 °C

Procedure

A solution of 24.5 g (0.085 mol) of N-(3-bromopropyl)-2-nitrobenzamide in 75 ml of dimethylformamide was slowly added to a solution of 7.00 g (0.10 mol) of tetrazole. The resulting solution was heated to 50° C. and allowed to react overnight. When the reaction was complete, as determined by thin layer chromatography, most of the dimethylformamide was removed under reduced pressure. The resultant residue was diluted with water, causing a precipitate to form. The precipitate was isolated by filtration and dried under vacuum. Thin layer chromatography and nuclear magnetic resonance spectroscopy indicated the presence of two isomers; namely, the N-1 and N-2 alkylated tetrazoles (75:25 ). The N-2 alkylated compound was isolated by column chromatography to provide 4.3 g of the desired subtitled intermediate. The N-1 alkylated compound was isolated by twice crystallizing the precipitate from cyanomethane to provide 3.72 g of that compound. (m.p. 148°-150° C.).

Workup

customto react overnight
customwas removed under reduced pressure
additionThe resultant residue was diluted with water
customto form
customThe precipitate was isolated by filtration
customdried under vacuum
customThe N-2 alkylated compound was isolated by column chromatography

Sources & evidence

ORD record: ord-6f00463f05e746d698995d339331fe6f
Source dataset: uspto-grants-1995_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05397798

Reaction notes

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