Bromoacetonitrile → HCID 9880293, compound

HRID 558257Notes

Reaction equation

HRID 558257 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]([CH:17]=[C:18]([Cl:20])[CH:19]=1)[O:7][C:8]1[C:9]([CH2:15][CH3:16])=[N:10][NH:11][C:12]=1[CH2:13][CH3:14].[H][H].Br[CH2:24][C:25]#[N:26]>CN(C)C=O>[Cl:3][C:4]1[CH:5]=[C:6]([CH:17]=[C:18]([Cl:20])[CH:19]=1)[O:7][C:8]1[C:12]([CH2:13][CH3:14])=[N:11][N:10]([CH2:24][C:25]#[N:26])[C:9]=1[CH2:15][CH3:16]

Participants

6

Reactant 4

HCID 11534BromoacetonitrileHCID 24758Sodium hydrideHCID 9878953HCID 9878953, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 9880293HCID 9880293, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Sodium hydride (60% dispersion in oil, 470 mg, 11.8 mmol) was added to a stirred solution of 4-(3,5-dichlorophenoxy)-3,5-diethyl-1H-pyrazole (3 g, 10.5 mmol, Example 3) in dry N,N-dimethylformamide (20 ml) at 0° C. under nitrogen. The mixture was stirred for 5 minutes during which time hydrogen was evolved and then bromoacetonitrile (0.81 ml, 11.6 mmol) was added. The yellow solution turned dark brown and a precipitate formed. Further dry N,N-dimethylformamide (5 ml) was added to aid dissolution and after 45 minutes the reaction mixture was quenched by the addition of water (1 ml). The mixture was partitioned between water (150 ml) and diethyl ether (2×150 ml). The combined organic layers were washed with water (50 ml) and brine (100 ml), dried over magnesium sulphate and concentrated under reduced pressure. The crude product was purified by flash chromatography on silica gel eluting with dichloromethane to provide the title compound (3.2 g) as a yellow powder, m.p. 70-72° C.

Workup

  1. customa precipitate formed
  2. customwas quenched by the addition of water (1 ml)
  3. customThe mixture was partitioned between water (150 ml) and diethyl ether (2×150 ml)
  4. washThe combined organic layers were washed with water (50 ml) and brine (100 ml)
  5. dry with materialdried over magnesium sulphate
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product was purified by flash chromatography on silica gel eluting with dichloromethane

Sources & evidence

ORD record
ord-447a7349880949438751c2c67510ea88
Source dataset
uspto-grants-2011_11
Patent number
US08063044B2

Reaction notes

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