Water → HCID 21395779, compound

HRID 258912Notes

Reaction equation

HRID 258912 reaction equation
[Cl:1][C:2]1[S:6][C:5]([C:7]([C:9]2[CH:14]=[CH:13][C:12]([CH:15](Br)[CH3:16])=[CH:11][CH:10]=2)=[O:8])=[CH:4][CH:3]=1.[C-:18]#[N:19].[Na+].O>O1CCOCC1>[Cl:1][C:2]1[S:6][C:5]([C:7]([C:9]2[CH:14]=[CH:13][C:12]([CH:15]([CH3:16])[C:18]#[N:19])=[CH:11][CH:10]=2)=[O:8])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 8929Sodium CyanideHCID 12232970HCID 12232970, compound

Product 1

HCID 21395779HCID 21395779, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 9.9 parts of α-bromo-α-methyl-p-tolyl 5-chloro-2-thienyl ketone, 1.96 parts of sodium cyanide, 12 parts of water and 48 parts of dioxane is stirred for 17 hours while heating at 90° C. The reaction is evaporated and 36 parts of water are added to the residue. The product is extracted with ether. The extract is dried and evaporated. The residue is purified by column-chromatography over silicagel, using chloroform as eluent. The pure fraction is collected and the eluent is evaporated. The residue is triturated in n-hexane, yielding p-(5-chloro-2-thenoyl)hydratroponitrile; mp. 90° C.

Workup

  1. customThe reaction is evaporated
  2. addition36 parts of water are added to the residue
  3. extractionThe product is extracted with ether
  4. customThe extract is dried
  5. customevaporated
  6. customThe residue is purified by column-chromatography over silicagel
  7. customThe pure fraction is collected
  8. customthe eluent is evaporated
  9. customThe residue is triturated in n-hexane

Sources & evidence

ORD record
ord-06bfcae605fb4d11ace7e39a7cce9919
Source dataset
uspto-grants-1977_07
Patent number
US04035376

Reaction notes

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