Azido(trimethyl)stannane → HCID 178423768, compound

HRID 248406Notes

Reaction equation

HRID 248406 reaction equation
[Cl:1][C:2]1[S:6][C:5]([C:7]#[N:8])=[C:4]([C:9]2[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=2)[CH:3]=1.C[Sn]([N:20]=[N+:21]=[N-:22])(C)C>C1(C)C(C)=CC=CC=1>[Cl:1][C:2]1[S:6][C:5]([C:7]2[NH:22][N:21]=[N:20][N:8]=2)=[C:4]([C:9]2[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=2)[CH:3]=1

Participants

4

Reactant 2

HCID 5104973Azido(trimethyl)stannaneHCID 19759322HCID 19759322, compound

Product 1

HCID 178423768HCID 178423768, compoundYield 265.8%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A mixture of 5-chloro-3-(4-methylphenyl)thiophene-2-carbonitrile (4.67 g), trimethyltin azide (12.3 g) and xylene (100 ml) was heated under reflux for 15 hours. After standing for 3 days at ambient temperature, the precipitate was collected by vacuum filtration to give 5-chloro-3-(4-methylphenyl)-2-(1H-tetrazol-5-yl)thiophene (14.7 g) as a yellowish powder. This powder was treated with trityl chloride (6.7 g) and 10N aqueous sodium hydroxide (2.4 ml) in dichloromethane (59 ml), and tetrahydrofuran (10 ml) at ambient temperature for 20 hours. The reaction mixture was washed with brine and dried over magnesium sulfate. The solvents were evaporated in vacuo to give a residue which was purified by silica gel column chromatography to afford 5-chloro-3-(4-methylphenyl)-2-(1-trityl-1H-tetrazol-5-yl)thiophene (10.3 g).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 15 hours
  3. filtrationthe precipitate was collected by vacuum filtration

Sources & evidence

ORD record
ord-d25032241dcf45adab59bf3614066939
Source dataset
uspto-grants-1993_05
Patent number
US05210092

Reaction notes

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