Trimethyltin chloride → HCID 178450427, compound

HRID 274253Notes

Reaction equation

HRID 274253 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH:16]([C:22](=[O:26])[CH2:23][CH2:24][CH3:25])[C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:11][CH:10]=1)#[N:2].C[Sn]([N:31]=[N+:32]=[N-:33])(C)C.[N-]=[N+]=[N-].[Na+].C[Sn](Cl)(C)C>C1(C)C=CC=CC=1>[NH:31]1[C:1]([C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[C:9]2[CH:14]=[CH:13][C:12]([CH2:15][CH:16]([C:22](=[O:26])[CH2:23][CH2:24][CH3:25])[C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:11][CH:10]=2)=[N:2][N:33]=[N:32]1

Participants

6

Reactant 4

HCID 14016Trimethyltin chlorideHCID 33557Sodium AzideHCID 5104973Azido(trimethyl)stannane2×HCID 10020734Ethyl 2-[(2'-cyanobiphenyl-4-yl)methyl]-3-oxohexanoate

Product 1

HCID 178450427HCID 178450427, compoundYield 73.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 69.9 g of ethyl 2-[(2'-cyanobiphenyl-4-yl)methyl]-3-oxohexanoate, prepared according to Example 5, 700 ml of anhydrous toluene and 47.5 g of trimethyltin azide, prepared from sodium azide and trimethyltin chloride, is refluxed for 24 h. A further 47.5 g of trimethyltin azide are added and reflux is continued for 16 h. The mixture is concentrated to 50%. The orange solution obtained is purified by chromatography twice in succession (eluent: chloroform 90%/methanol 10%, then chloroform 95%/methanol 5%) to give 58 g of an orange oil, which crystallizes.

Workup

  1. customprepared
  2. temperatureis refluxed for 24 h
  3. temperaturereflux
  4. concentrationThe mixture is concentrated to 50%
  5. customThe orange solution obtained
  6. customis purified by chromatography twice in succession (eluent

Sources & evidence

ORD record
ord-6c634aa6705a413eb0d85c95b8623657
Source dataset
uspto-grants-1995_02
Patent number
US05389632

Reaction notes

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