Tributyltin azide → HCID 178526988, compound

HRID 1494135Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][CH:16]([CH2:21][CH2:22][CH2:23][C:24]2[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=2)[CH2:17][CH2:18][C:19]#[N:20])(=[O:10])=[O:9])=[CH:4][CH:3]=1.C([Sn]([N:43]=[N+:44]=[N-:45])(CCCC)CCCC)CCC>O1CCCC1>[OH2:9].[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][CH:16]([CH2:21][CH2:22][CH2:23][C:24]2[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=2)[CH2:17][CH2:18][C:19]2[NH:45][N:44]=[N:43][N:20]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][CH:16]([CH2:21][CH2:22][CH2:23][C:24]2[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=2)[CH2:17][CH2:18][C:19]2[NH:45][N:44]=[N:43][N:20]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of 0.528 g 8-(p-chlorophenylsulfonamido)-4[3-(3-pyridyl)propyl]octanenitrile and 1.04 mL tributyltin azide in 5 mL tetrahydrofuran is heated at 120° C. for 64 hours. The solvent is evaporated and subjected to flash chromatography over silica gel using methylene chloride/hexane/methanol/acetic acid (45:25:5:0.8) as eluent to give an oil which is purified again by preparative thin layer chromatography using methylene chloride, methanol, hexane, acetic acid (45:5:25:0.8) as eluent to yield an oil which is triturated with ether and hexane to give 5-{7-(p-chlorophenylsulfonamido)-3-[3-(3-pyridyl)-propyl]-heptyl}-1H-tetrazole hemihydrate, m.p. 56-81°.

Workup

customThe solvent is evaporated
customto give an oil which
customis purified again by preparative thin layer chromatography
customto yield an oil which
customis triturated with ether and hexane

Sources & evidence

ORD record: ord-9870962f62234ed58e27fd0509505d39
Source dataset: uspto-grants-1991_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05025025

Reaction notes

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