Water → HCID 73446014, compound

HRID 1868291Notes

Reaction equation

HRID 1868291 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].O.[C:6]([C:8]([C:13]1[S:14][CH:15]=[CH:16][CH:17]=1)=[CH:9][C:10](Cl)=[O:11])#[N:7]>O1CCOCC1>[C:6]([C:8]([C:13]1[S:14][CH:15]=[CH:16][CH:17]=1)=[CH:9][C:10]([N:1]=[N+:2]=[N-:3])=[O:11])#[N:7]

Participants

5

Reactant 3

HCID 962Water2×HCID 33557Sodium AzideHCID 73446015HCID 73446015, compound

Product 1

HCID 73446014HCID 73446014, compoundYield 97.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a vigorously stirring suspension of NaN3 (55 g, 0.85 mol) in 1:1; dioxane:H2O (200 mL) cooled to 0° C. was added dropwise over 20 min a solution of 3-cyano-3-thiophen-2-yl-acryloyl chloride 22 (84.3 g, 0.428 mol) in dioxane (150 mL). After stirring at 0° C. for 20 min, the reaction was warmed to room temperature and stirred for 1 h. To the reaction solution was added 600 mL H2O, thus producing a precipitate which was filtered, washed with H2O and dried under vacuum to provide pure 85 g of 23.

Workup

  1. stirringAfter stirring at 0° C. for 20 min
  2. stirringstirred for 1 h
  3. customthus producing a precipitate which
  4. filtrationwas filtered
  5. washwashed with H2O
  6. customdried under vacuum

Sources & evidence

ORD record
ord-0a4ef43ad62e469b8a23c595fcfd7835
Source dataset
uspto-grants-2009_12
Patent number
US07635695B2

Reaction notes

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