Hydrogen Bromide → HCID 20562656, compound

HRID 1155044Notes

Reaction equation

HRID 1155044 reaction equation
[CH2:1]([C:3]1[N:12]([CH2:13][CH2:14][CH2:15]OC2C=CC=CC=2)[C:11]2[C:10](=[O:23])[N:8]([CH3:9])[C:7](=[O:24])[N:6]([CH3:25])[C:5]=2[N:4]=1)[CH3:2].[OH-].[Na+].[BrH:28]>>[Br:28][CH2:15][CH2:14][CH2:13][N:12]1[C:11]2[C:10](=[O:23])[N:8]([CH3:9])[C:7](=[O:24])[N:6]([CH3:25])[C:5]=2[N:4]=[C:3]1[CH2:1][CH3:2]

Participants

4

Reactant 3

HCID 260Hydrogen BromideHCID 14798Sodium HydroxideHCID 20562623HCID 20562623, compound

Product 1

HCID 20562656HCID 20562656, compoundYield 82%

Procedure

A mixture of 8-ethyl-7-(3-phenoxypropyl)theophylline (23.0 g; 0.067 M) and 48% aqueous hydrogen bromide (150 ml) was heated at reflux for 20 hours. The mixture was cooled and poured into dilute aqueous sodium hydroxide solution. The suspension was extracted with chloroform and the organic phase was washed with water, aqueous 10% sodium hydroxide solution and water and was dried (MgSO4), filtered and the filtrate was evaporated to dryness leaving a colourless solid. This solid was crystallised from ethanol to give the required compound as colourless prisms, (8.2 g) (82%) mp 119°-120°.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 20 hours
  3. temperatureThe mixture was cooled
  4. extractionThe suspension was extracted with chloroform
  5. washthe organic phase was washed with water, aqueous 10% sodium hydroxide solution and water
  6. dry with materialwas dried (MgSO4)
  7. filtrationfiltered
  8. customthe filtrate was evaporated to dryness
  9. customleaving a colourless solid
  10. customThis solid was crystallised from ethanol

Sources & evidence

ORD record
ord-cf77c9eb94694cbf98ea2bad90a96350
Source dataset
uspto-grants-1981_11
Patent number
US04299832

Reaction notes

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