Hydrochloric Acid → HCID 178439659, compound

HRID 1194684Notes

Reaction equation

HRID 1194684 reaction equation
[C:1]([C:4]1[CH:24]=[CH:23][C:7]([O:8][CH2:9][C:10]2[C:15]3=[N:16][CH:17]=[C:18]([C:21]#[N:22])[C:19](=[O:20])[N:14]3[CH:13]=[CH:12][CH:11]=2)=[C:6]([CH2:25][CH2:26][CH3:27])[C:5]=1[OH:28])(=[O:3])[CH3:2].[Cl-].[Al+3].[Cl-].[Cl-].[N-:33]=[N+:34]=[N-:35].[Na+].Cl>O1CCCC1>[C:1]([C:4]1[CH:24]=[CH:23][C:7]([O:8][CH2:9][C:10]2[C:15]3=[N:16][CH:17]=[C:18]([C:21]4[NH:35][N:34]=[N:33][N:22]=4)[C:19](=[O:20])[N:14]3[CH:13]=[CH:12][CH:11]=2)=[C:6]([CH2:25][CH2:26][CH3:27])[C:5]=1[OH:28])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 33557Sodium AzideHCID 6451240Aluminum(III) ChlorideHCID 14130379HCID 14130379, compound

Product 1

HCID 178439659HCID 178439659, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of l.00 g (2.65 mmoles) of 9-[(4-acetyl-3-hydroxy-2-n-propylphenoxy)methyl]-3-cyano-4H-pyrido[1,2-a]pyrimidin-4-one, 0.97 g (7.27 mmoles) of aluminum chloride, 1.43 g (21.99 mmoles) of sodium azide and 20 ml of tetrahydrofuran was heated under reflux for 2 hours. After cooling, the resulting reaction solution was diluted with ice water and then acidified with dilute hydrochloric acid. The precipitate so formed was collected by filtration and recrystallized from dimethyformamide to obtain 0.72 g (65% yield) of 9-[(4-acetyl-3-hydroxy-2-n-propylphenoxy)methyl]-3-(1H-tetrazol-5-yl)-4H-pyrido[1,2-a]-pyrimidin-4-one in the form of white crystals. These crystals had a melting point of 269°-271° C. (dec.).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2 hours
  3. temperatureAfter cooling
  4. customthe resulting reaction solution
  5. customThe precipitate so formed
  6. filtrationwas collected by filtration
  7. customrecrystallized from dimethyformamide

Sources & evidence

ORD record
ord-ccb522d355c64299aa13218c18fa93fa
Source dataset
uspto-grants-1989_03
Patent number
US04816459

Reaction notes

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