Sodium Azide → 3-Chloro-N-isopropyl-5-methoxy-N-[2-(1-methyl-1H-tetrazol-5-yl)ethyl]-benzamide

HRID 2268600Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([CH:17]=[C:18]([O:20][CH3:21])[CH:19]=1)[C:5]([N:7]([CH:14]([CH3:16])[CH3:15])[CH2:8][CH2:9][C:10](=O)[NH:11][CH3:12])=[O:6].[N-:22]=[N+:23]=[N-:24].[Na+].FC(F)(F)S(OS(C(F)(F)F)(=O)=O)(=O)=O>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:17]=[C:18]([O:20][CH3:21])[CH:19]=1)[C:5]([N:7]([CH:14]([CH3:16])[CH3:15])[CH2:8][CH2:9][C:10]1[N:11]([CH3:12])[N:24]=[N:23][N:22]=1)=[O:6]

Participants

Conditions

Temperature: 0 °C

Procedure

To a stirred solution of 3-chloro-N-isopropyl-5-methoxy-N-(2-methylcarbamoyl-ethyl)-benzamide (0.312 g) in anhydrous dichloromethane (5.0 ml) was added sodium azide (0.065 g) and the mixture cooled to 0° C. Trifluoromethanesulphonic anhydride (0.200 ml) was added and the reaction stirred at room temperature for 18 h. The reaction mixture was partitioned between ethyl acetate and water. The aqueous layer was removed and the organic layer dried with brine and over sodium sulphate and concentrated under reduced pressure. The residue was purified by flash column chromatography, eluting with ethyl acetate:petroleum ether (4:1 v/v); to give the title compound as a white solid (0.121 g).

Workup

customThe reaction mixture was partitioned between ethyl acetate and water
customThe aqueous layer was removed
dry with materialthe organic layer dried with brine and over sodium sulphate
concentrationconcentrated under reduced pressure
customThe residue was purified by flash column chromatography
washeluting with ethyl acetate:petroleum ether (4:1 v/v)

Sources & evidence

ORD record: ord-cd1a111fc0484ae7969a99fa6268286e
Source dataset: uspto-grants-2001_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06326386B1

Reaction notes

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