Sodium hydride → HCID 53893541, compound

HRID 1729464Notes

Reaction equation

HRID 1729464 reaction equation
[H-].[Na+].[CH2:3]([C:7]1[NH:8][C:9]([CH:13]=[O:14])=[C:10]([Cl:12])[N:11]=1)[CH2:4][CH2:5][CH3:6].Br[CH2:16][C:17]1[CH:30]=[CH:29][C:28]2[C:19](=[CH:20][C:21]3[C:26]([CH:27]=2)=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH:18]=1>CN(C=O)C>[CH2:3]([C:7]1[N:8]([CH2:16][C:17]2[CH:30]=[CH:29][C:28]3[C:19](=[CH:20][C:21]4[C:26]([CH:27]=3)=[CH:25][CH:24]=[CH:23][CH:22]=4)[CH:18]=2)[C:9]([CH:13]=[O:14])=[C:10]([Cl:12])[N:11]=1)[CH2:4][CH2:5][CH3:6]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 190129612-(Bromomethyl)anthraceneHCID 178418251HCID 178418251, compound

Product 1

HCID 53893541HCID 53893541, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
60 °C

Procedure

Sodium hydride (50% dispersion in oil, 1.37 g, 28.6 mmol, 1.1 eq) was added to a DMF solution (50 mL) containing 2-n-butyl-4-chloroimidazole-5-carboxaldehyde (prepared as in European Patent Application Number 89100144.8, published 7.19.89) (4.85 g, 26.0 mmol, 1.0 eq). The contents were heated with stirring at 60° C. until everything was dissolved. The reaction was then cooled to 0° C. and a DMF solution (75 mL) of 2-bromomethylanthracene (entire contents from the previous step: 7.77 g of impure material, theoretically 26.0 mmol, 1.0 eq) was added and the entire contents stirred at room temperature overnight. The solvent was removed in vacuo and the residue flash chromatographed in 9:1 toluene/ethyl acetate to 75:25 toluene/ethyl acetate to yield 3.73 g of an amber glass. This material could not be crystallized and was used without further purification for the next step. NMR (CDCl3): δ 9.80 (s, 1H); 8.40 (s, 1H); 8.33 (s, 1H); 7.98 (m, 3H); 7.48 (m, 3H); 7.23 (m, 1H); 5.72 (s, 2H); 2.79 (t, 2H, J=7Hz); 1.69 (t of t, 2H, J=7,7Hz); 1.33 (t of q, 2H, J=7,7Hz); 0.84 (t, 3H, J=7Hz). ##STR56##

Workup

  1. temperatureThe contents were heated
  2. dissolutionwas dissolved
  3. temperatureThe reaction was then cooled to 0° C.
  4. stirringthe entire contents stirred at room temperature overnight
  5. customThe solvent was removed in vacuo
  6. customthe residue flash chromatographed in 9:1 toluene/ethyl acetate to 75:25 toluene/ethyl acetate

Sources & evidence

ORD record
ord-e192eabfa876435bb3bc30f023fe84c5
Source dataset
uspto-grants-1994_07
Patent number
US05332820

Reaction notes

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