Water → HCID 70231174, compound

HRID 1420735Notes

Reaction equation

HRID 1420735 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-99c4153ed51d41a3ab6602bc4763dc2d
Source dataset
uspto-grants-2000_06
Patent number
US06071934

Reaction notes

Loading…