Sodium Cyanide → 2-(2-Bromo-1,3-thiazol-4-yl)acetonitrile

HRID 44668Notes

Reaction equation

HRID 44668 reaction equation
[Br:1][C:2]1[S:3][CH:4]=[C:5]([CH2:7]I)[N:6]=1.[C-:9]#[N:10].[Na+]>CS(C)=O.C(OCC)C.O>[Br:1][C:2]1[S:3][CH:4]=[C:5]([CH2:7][C:9]#[N:10])[N:6]=1

Participants

5

Reactant 2

HCID 8929Sodium CyanideHCID 666435272-Bromo-4-(iodomethyl)thiazole

Product 1

HCID 666434812-(2-Bromo-1,3-thiazol-4-yl)acetonitrileYield 86%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 21584184Diethylether waterSolvent

Procedure

A solution of 2-bromo-4-(iodomethyl)thiazole (2.11 g, 6.942 mmol) in DMSO (15 mL) under nitrogen was treated with sodium cyanide (345.0 mg, 7.039 mmol) and allowed to stir for 40 minutes. The reaction was diluted with diethyl ether/water and the layers separated, the aqueous was extracted further with ether (2×) and the combined organics washed with brine, dried (Na2SO4), filtered and concentrated. The resultant residue was purified by column chromatography (3:1 Petroleum ether/EtOAc) to afford the product as a white solid (1.20 g, 86% Yield). 1H NMR (CDCl3, 400 MHz) δ 3.91 (2H, s), 7.31 (1H, s); MS (ES+) 204.95

Workup

  1. customthe layers separated
  2. extractionthe aqueous was extracted further with ether (2×)
  3. washthe combined organics washed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe resultant residue was purified by column chromatography (3:1 Petroleum ether/EtOAc)

Sources & evidence

ORD record
ord-d5ffa49f019d41dd9201e406159f7804
Source dataset
uspto-grants-2013_09
Patent number
US08541445B2

Reaction notes

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