Water → HCID 21395779, compound

HRID 1439564Notes

Reaction equation

HRID 1439564 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 mixture 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 silica gel, 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 mixture 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 silica gel
  7. customThe pure fraction is collected
  8. customthe eluent is evaporated
  9. customThe residue is triturated in n-hexane

Sources & evidence

ORD record
ord-e9fe40dd3d8b4a4390728789118ee89e
Source dataset
uspto-grants-1977_11
Patent number
US04060528

Reaction notes

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