Tributyltin azide → HCID 178526988, compound

HRID 465595Notes

Reaction equation

HRID 465595 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

4

Reactant 2

HCID 4984872Tributyltin azideHCID 10342851HCID 10342851, compound

Product 1

HCID 178526988HCID 178526988, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

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° for 64 h. 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/hexane/methanol/acetic acid (45:25:5:0.8) 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

  1. temperatureis heated at 120° for 64 h
  2. customThe solvent is evaporated
  3. customto give an oil which
  4. customis purified again by preparative thin layer chromatography
  5. customto yield an oil which
  6. customis triturated with ether and hexane

Sources & evidence

ORD record
ord-c31229d548d645bcab977a5a4419a002
Source dataset
uspto-grants-1992_10
Patent number
US05153214

Reaction notes

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