Tributyltin azide → HCID 178469305, compound

HRID 462450Notes

Reaction equation

HRID 462450 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH:9]1[C:14]([C:15]([O:17][CH3:18])=[O:16])=[C:13]([CH3:19])[NH:12][C:11]([CH2:20][O:21][CH2:22][C:23]#[N:24])=[C:10]1[C:25]([O:27][CH2:28][CH3:29])=[O:26].C([Sn]([N:43]=[N+:44]=[N-:45])(CCCC)CCCC)CCC>O1CCOCC1>[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH:9]1[C:14]([C:15]([O:17][CH3:18])=[O:16])=[C:13]([CH3:19])[NH:12][C:11]([CH2:20][O:21][CH2:22][C:23]2[NH:45][N:44]=[N:43][N:24]=2)=[C:10]1[C:25]([O:27][CH2:28][CH3:29])=[O:26]

Participants

4

Reactant 2

HCID 4984872Tributyltin azideHCID 13457227HCID 13457227, compound

Product 1

HCID 178469305HCID 178469305, compoundYield 81.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of [4-(2,3-dichlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-1,4-dihydropyridin-2-yl]methoxyacetonitrile (3.52 g) and tri-n-butyltin azide (3.00 g) in dioxane (100 ml) was heated under reflux for 21.5 hours and then evaporated. The residual oil was taken up in diethyl ether (200 ml) and dry hydrogen chloride was bubbled through the stirred solution in a slow stream for 50 minutes. The resulting precipitate was collected, washed with diethyl ether and dried to give the title compound (3.14 g), m.p. 112°-114° C.

Workup

  1. temperatureunder reflux for 21.5 hours
  2. customevaporated
  3. customdry hydrogen chloride was bubbled through the stirred solution in a slow stream for 50 minutes
  4. customThe resulting precipitate was collected
  5. washwashed with diethyl ether
  6. customdried

Sources & evidence

ORD record
ord-8dad4257a154445d9684562544a554c7
Source dataset
uspto-grants-1985_05
Patent number
US04515799

Reaction notes

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