Tributyltin azide → HCID 178527471, compound

HRID 631870Notes

Reaction equation

HRID 631870 reaction equation
[Br:1][C:2]1[C:3]([C:18]#[N:19])=[C:4]([NH:8][S:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)(=[O:11])=[O:10])[CH:5]=[CH:6][CH:7]=1.C([Sn]([N:33]=[N+:34]=[N-:35])(CCCC)CCCC)CCC>ClC1C=CC=CC=1Cl.CCOCC>[Br:1][C:2]1[C:3]([C:18]2[NH:35][N:34]=[N:33][N:19]=2)=[C:4]([NH:8][S:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)(=[O:11])=[O:10])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 4984872Tributyltin azideHCID 68296415HCID 68296415, compound2×

Product 1

HCID 178527471HCID 178527471, compoundYield 76.6%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 72391,2-DichlorobenzeneSolvent

Procedure

A solution of N-(3-Bromo-2-cyanophenyl)-benzenesulfonamide (Intermediate 21, 0.22 g) and tributyltin azide (0.43 g) in 1,2-dichlorobenzene (1.5 mL) was heated by microwave irradiation at 130° C. for 2 hours. The mixture was diluted with ether and extracted with aqueous 1M sodium hydroxide. The aqueous solution was acidified with 1N hydrochloric acid to pH 1 and then extracted with ethyl acetate. The organic solution was washed with brine and then dried with sodium sulfate, filtered and the filtrate was evaporated. The residue was triturated with ether and the solid was collected by filtration to give the title compound as a colorless solid (0.19 g).

Workup

  1. extractionextracted with aqueous 1M sodium hydroxide
  2. extractionextracted with ethyl acetate
  3. washThe organic solution was washed with brine
  4. dry with materialdried with sodium sulfate
  5. filtrationfiltered
  6. customthe filtrate was evaporated
  7. customThe residue was triturated with ether
  8. filtrationthe solid was collected by filtration

Sources & evidence

ORD record
ord-0c5f294abe5a46008a034aa27a8ebcc1
Source dataset
uspto-grants-2016_04
Patent number
US09321740B2

Reaction notes

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