Water → 1159511-94-0

HRID 1423101Notes

Reaction equation

HRID 1423101 reaction equation
Br[CH2:2][C:3]1[O:7][C:6]([CH3:8])=[N:5][CH:4]=1.[C-:9]#[N:10].[Na+].O>CN(C=O)C>[CH3:8][C:6]1[O:7][C:3]([CH2:2][C:9]#[N:10])=[CH:4][N:5]=1

Participants

5

Reactant 3

HCID 962WaterHCID 8929Sodium CyanideHCID 128087865-(Bromomethyl)-2-methyloxazole

Product 1

HCID 441196091159511-94-0

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

A solution of 5-(bromomethyl)-2-methyl-oxazole CAS [82190-68-9] (15 g, 85 mmol) in DMF (150 mL) was treated with NaCN (10.4 g, 213 mmol) at room temperature and the mixture stirred at 70° C. for 1 h. After this time the mixture was poured onto ice-cooled water (300 mL) and extracted with CH2Cl2 (5×200 mL). The combined organic extracts were then washed with brine, dried with Na2SO4 for 30 min, and the mixture concentrated to afford crude 2-methyl-5-oxazoleacetonitrile product CAS [1159511-94-0] (10 g).

Workup

  1. additionAfter this time the mixture was poured onto ice-
  2. extractionextracted with CH2Cl2 (5×200 mL)
  3. washThe combined organic extracts were then washed with brine
  4. dry with materialdried with Na2SO4 for 30 min
  5. concentrationthe mixture concentrated

Sources & evidence

ORD record
ord-1cbcc4579cd64f388e091033012f9d46
Source dataset
uspto-grants-2015_01
Patent number
US08927546B2

Reaction notes

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