Azido(trimethyl)stannane → HCID 178423717, compound

HRID 323176Notes

Reaction equation

[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([C:14]([NH:16][C:17]3[CH:34]=[CH:33][C:20]([C:21]([N:23]([CH3:32])[C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=4[C:30]#[N:31])=[O:22])=[CH:19][CH:18]=3)=[O:15])=[CH:10][CH:11]=[CH:12][CH:13]=2)=[CH:4][CH:3]=1.C[Sn]([N:39]=[N+:40]=[N-:41])(C)C>C1(C)C(C)=CC=CC=1.C(Cl)(Cl)Cl>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:9]([C:14]([NH:16][C:17]3[CH:18]=[CH:19][C:20]([C:21]([N:23]([CH3:32])[C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=4[C:30]4[NH:41][N:40]=[N:39][N:31]=4)=[O:22])=[CH:33][CH:34]=3)=[O:15])=[CH:10][CH:11]=[CH:12][CH:13]=2)=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of 4-(4′-methylbiphenyl-2-carboxamido)-N-methyl-N-(2-cyanophenyl)benzamide (350 mg) and trimethyltin azide (453 mg) in xylene (15 ml) heated at 120° C. for 2 days and cooled to ambient temperature. The solution was directly applied to silica gel column (the column was pre-packed with chloroform as a solvent). The column was eluted with 2% methanol in chloroform and the solvent was evaporated in vacuo. The residue was solidified with diethyl ether to give 4-(4′-methylbiphenyl-2-carboxamido)-N-methyl-N-[2-(tetrazol-5-yl)phenyl]benzamide (233 mg) as a white powder.

Workup

temperaturecooled to ambient temperature
washThe column was eluted with 2% methanol in chloroform
customthe solvent was evaporated in vacuo

Sources & evidence

ORD record: ord-61441e7485c0499fb0f170acf0905115
Source dataset: uspto-grants-2001_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06211242B1

Reaction notes

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