Water → HCID 59442520, compound

HRID 657519Notes

Reaction equation

HRID 657519 reaction equation
[H-].[Na+].[Cl:3][C:4]1[NH:8][CH:7]=[N:6][C:5]=1[CH3:9].Br[CH2:11][CH:12]1[CH2:14][CH2:13]1.O>CCCCC.CN(C=O)C.CC(=O)OCC>[Cl:3][C:4]1[N:8]=[CH:7][N:6]([CH2:11][CH:12]2[CH2:14][CH2:13]2)[C:5]=1[CH3:9].[Cl:3][C:4]1[N:8]([CH2:11][CH:12]2[CH2:14][CH2:13]2)[CH:7]=[N:6][C:5]=1[CH3:9]

Participants

9

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 81503BromomethylcyclopropaneHCID 178433268HCID 178433268, compound

Product 2

HCID 59442520HCID 59442520, compoundHCID 59442658HCID 59442658, compound

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolvent2×HCID 8003PentaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

4.7 g (118 mmol) of sodium hydride (60% strength in mineral oil) were washed with pentane under a nitrogen atmosphere, suspended in 100 ml of DMF and cooled to 0° C. A solution of 12.5 g (107 mmol) of 5-chloro-4-methyl-1H-imidazole in 100 ml of DMF was added. Then 5.5 g of bromomethylcyclopropane were added and the mixture was stirred for 16 h at 20° C. 250 ml of water and EA were added, the phases were separated and the aqueous layer was extracted with EA. The combined organic phases were washed with brine and dried over sodium sulfate. The solvent was removed in vacuo. Flash chromatography (silica gel; EA/HEP, gradient from 20:80 to 40:60) of the residue yielded 7.5 g of 4-chloro-1-cyclopropylmethyl-5-methyl-1H-imidazole as an oil and 3.6 g of 5-chloro-1-cyclopropylmethyl-4-methyl-1H-imidazole as an oil.

Workup

  1. customthe phases were separated
  2. extractionthe aqueous layer was extracted with EA
  3. washThe combined organic phases were washed with brine
  4. dry with materialdried over sodium sulfate
  5. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-ae4b8d94ee49485eae3e5f792b36e175
Source dataset
uspto-grants-2011_12
Patent number
US08076324B2

Reaction notes

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