Sodium Cyanide → HCID 68601548, compound

HRID 1799681Notes

Reaction equation

HRID 1799681 reaction equation
Cl[CH2:2][C:3]1[N:4]=[CH:5][S:6][C:7]=1/[CH:8]=[CH:9]\[S:10][C:11]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[C-:30]#[N:31].[Na+]>CN(C=O)C.[Cl-].[Na+].O>[C:30]([CH2:2][C:3]1[N:4]=[CH:5][S:6][C:7]=1/[CH:8]=[CH:9]\[S:10][C:11]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)#[N:31]

Participants

5

Reactant 2

HCID 8929Sodium CyanideHCID 68601237HCID 68601237, compound

Product 1

HCID 68601548HCID 68601548, compoundYield 38.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A suspension of 350 mg of 4-chloromethyl-5-((Z)-2-tritylthioethen-1-yl)thiazole, prepared in step a) in Example 2, in 7 ml of DMF was cooled in ice, and 94 mg of sodium cyanide was added to the cooled suspension under an argon atmosphere. The mixture was stirred at room temperature for 2.5 hr, and brine was then added to the reaction solution. The mixture was extracted twice with ethyl acetate, and the organic layers were combined, followed by washing with brine. The washed organic layer was dried over anhydrous magnesium sulfate, was filtered, and was concentrated under the reduced pressure. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate=5:1) to give 132 mg of the title compound.

Workup

  1. customprepared in step a) in Example 2
  2. extractionThe mixture was extracted twice with ethyl acetate
  3. washby washing with brine
  4. dry with materialThe washed organic layer was dried over anhydrous magnesium sulfate
  5. filtrationwas filtered
  6. concentrationwas concentrated under the reduced pressure
  7. customThe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=5:1)

Sources & evidence

ORD record
ord-91a041d040b3413f80ce4085324bc603
Source dataset
uspto-grants-2013_01
Patent number
US08344154B2

Reaction notes

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