Water → HCID 70231174, compound

HRID 2371491Notes

Reaction equation

HRID 2371491 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)/[C:7](=[CH:11]\[C:12]1[CH:17]=[CH:16][C:15]([S:18][CH3:19])=[CH:14][CH:13]=1)/[C:6]([CH3:20])=[C:5]2[CH2:21][CH2:22]I.[C-:24]#[N:25].[K+].O>CN(C=O)C.[Cl-].[Na+].O>[C:24]([CH2:22][CH2:21][C:5]1[C:4]2[C:8](=[CH:9][CH:10]=[C:2]([F:1])[CH:3]=2)/[C:7](=[CH:11]\[C:12]2[CH:17]=[CH:16][C:15]([S:18][CH3:19])=[CH:14][CH:13]=2)/[C:6]=1[CH3:20])#[N:25]

Participants

6

Reactant 3

HCID 962WaterHCID 9032Potassium CyanideHCID 70229083HCID 70229083, compound

Product 1

HCID 70231174HCID 70231174, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A mixture of the iodide from Step 1 (3.7 g, 8.5 mmol) and potassium cyanide (5.5 g, 85 mmol) in DMF (40 mL) was stirred at room temperature for 45 minutes. There was added water (50 mL) and brine (100 mL) and the mixture was extracted with 1:1 ethyl acetate-hexane (4×100 mL); the combined extracts were washed with water (2×50 mL) and brine (1×50 mL), dried and evaporated. The crude residue was chromatographed on silica gel eluting with a 1:2 mixture of ether-ethyl acetate to afford the title compound as a yellow oil.

Workup

  1. extractionthe mixture was extracted with 1:1 ethyl acetate-hexane (4×100 mL)
  2. washthe combined extracts were washed with water (2×50 mL) and brine (1×50 mL)
  3. customdried
  4. customevaporated
  5. customThe crude residue was chromatographed on silica gel eluting with a 1:2 mixture of ether-ethyl acetate

Sources & evidence

ORD record
ord-43f676dd298a41cfa19aa6904d998928
Source dataset
uspto-grants-1992_03
Patent number
US05093356

Reaction notes

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