Allyl bromide → HCID 21329311, compound

HRID 614352Notes

Reaction equation

HRID 614352 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]2[N:8]([C:12]3[CH:17]=[CH:16][C:15]4[O:18][CH2:19][O:20][C:14]=4[CH:13]=3)[C:9](=[O:11])[NH:10][C:5]2=[CH:4][CH:3]=1.[OH-].[K+].[CH2:23](Br)[CH:24]=[CH2:25]>CC(C)=O>[CH2:25]([N:10]1[C:5]2[C:6](=[N:7][C:2]([Cl:1])=[CH:3][CH:4]=2)[N:8]([C:12]2[CH:17]=[CH:16][C:15]3[O:18][CH2:19][O:20][C:14]=3[CH:13]=2)[C:9]1=[O:11])[CH:24]=[CH2:23]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 14797Potassium HydroxideHCID 54270804HCID 54270804, compound

Product 1

HCID 21329311HCID 21329311, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a stirred suspension of 4.6 g. (0.016 mole) of the imidazopyridine product of Step C in 175 ml. of acetone, was added 1.8 g. (0.032 mole) of powdered potassium hydroxide. After stirring at room temperature for 20 minutes, 3.9 g. (0.032 mole) of allylbromide was added. Stirring at room temperature was continued overnight and the mixture then was concentrated to one-half volume. The concentrate was diluted with 150 ml. of water and the crude product was collected by filtration. The crude product was crystallized from 70 ml. of ethanol giving 2.0 g. of needles melting at 146°-148° C.

Workup

  1. additionTo a stirred suspension of 4.6 g
  2. stirringStirring at room temperature
  3. waitwas continued overnight
  4. concentrationthe mixture then was concentrated to one-half volume
  5. additionThe concentrate was diluted with 150 ml
  6. filtrationof water and the crude product was collected by filtration
  7. customThe crude product was crystallized from 70 ml

Sources & evidence

ORD record
ord-e4699a2cc75d4c08b7f97b5e8bab0889
Source dataset
uspto-grants-1979_03
Patent number
US04144341

Reaction notes

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