Acetone → HCID 19006193, compound

HRID 1461177Notes

Reaction equation

HRID 1461177 reaction equation
[OH:1][C:2]1[C:3]([I:8])=[N:4][CH:5]=[CH:6][CH:7]=1.[CH2:9]([C:21]1[CH:28]=[CH:27][C:24]([CH2:25][Br:26])=[CH:23][CH:22]=1)[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20].CC(C)=O>S1(CCCC1)(=O)=O>[Br-:26].[OH:1][C:2]1[C:3]([I:8])=[N+:4]([CH2:25][C:24]2[CH:27]=[CH:28][C:21]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])=[CH:22][CH:23]=2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 180AcetoneHCID 971792-Iodopyridin-3-olHCID 19006202HCID 19006202, compound

Product 1

HCID 19006193HCID 19006193, compoundYield 80.3%

Reagents, catalysts & solvents 1

HCID 31347SulfolaneSolvent

Procedure

A mixture of 3-hydroxy-2-iodopyridine (22.1 g, 0.1M) and 4-dodecylbenzyl bromide (37.2 g, 0.101M) was stirred in sulpholane (100 ml) at 90° C. for 8 hours. Acetone was added and the precipitated product filtered and washed with acetone to yield a white solid (45 g). The product was recrystallised from a mixture of methanol and water, collected and dried at 60° C. (35 g).

Workup

  1. filtrationthe precipitated product filtered
  2. washwashed with acetone

Sources & evidence

ORD record
ord-1aa3031198b14e1ca886e709056d72d3
Source dataset
uspto-grants-1991_12
Patent number
US05074911

Reaction notes

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