Ethoxyacetyl chloride → HCID 67228629, compound

HRID 2383167Notes

Reaction equation

HRID 2383167 reaction equation
[CH2:1]([O:3][CH2:4][C:5](Cl)=O)[CH3:2].[CH2:8]([O:15][C:16]1[CH:17]=[C:18]2[C:23](=[CH:24][CH:25]=1)[N:22]1[N:26]=[N:27][N:28]=[C:21]1[C:20]([NH2:29])=[C:19]2[NH:30][CH2:31][CH:32]([CH3:34])[CH3:33])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>N1C=CC=CC=1>[CH2:8]([O:15][C:16]1[CH:17]=[C:18]2[C:23](=[CH:24][CH:25]=1)[N:22]1[N:26]=[N:27][N:28]=[C:21]1[C:20]1[N:29]=[C:5]([CH2:4][O:3][CH2:1][CH3:2])[N:30]([CH2:31][CH:32]([CH3:34])[CH3:33])[C:19]2=1)[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 84189Ethoxyacetyl chloride2×HCID 67227906HCID 67227906, compound

Product 1

HCID 67228629HCID 67228629, compoundYield 97.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Ethoxyacetyl chloride (2.7 g, 22 mmol) was added dropwise to a solution of 7-(benzyloxy)-N5-(2-methylpropyl)tetraazolo[1,5-a]quinoline-4,5-diamine (7.6 g, 21 mmol) in 200 mL of pyridine. The solution was stirred for 1 hour and additional ethoxyacetyl chloride was added. The solution was refluxed overnight, after which the solvent was removed. The solid material was dissolved in 300 mL of chloroform and stirred with 150 mL of 1% aqueous sodium carbonate. The pH was adjusted to 10 with 10% sodium hydroxide. The organic fraction was washed with 2 portions of 1% sodium carbonate and once with brine solution. The organic fraction was then dried over sodium sulfate and concentrated to give 8.8 g of 8-(benzyloxy)-5-(ethoxymethyl)-6-(2-methylpropyl)-6H-imidazo[4,5-c]tetraazolo[1,5-a]quinoline as a tan solid. A small portion was recrystallized from ethanol to provide an analytical sample, mp 183.5-184.5° C.

Workup

  1. temperatureThe solution was refluxed overnight
  2. customafter which the solvent was removed
  3. dissolutionThe solid material was dissolved in 300 mL of chloroform
  4. stirringstirred with 150 mL of 1% aqueous sodium carbonate
  5. washThe organic fraction was washed with 2 portions of 1% sodium carbonate and once with brine solution
  6. dry with materialThe organic fraction was then dried over sodium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-48ff0d0bd32244d1bc914dd7c567b611
Source dataset
uspto-grants-2012_09
Patent number
US08263594B2

Reaction notes

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