Hydrogen Bromide → HCID 19883096, compound

HRID 846587Notes

Reaction equation

HRID 846587 reaction equation
[N:1]1([S:7]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([O:16]CC3C=CC=CC=3)[N:11]=2)(=[O:9])=[O:8])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.Br>C(O)(=O)C>[N:1]1([S:7]([C:10]2[NH:11][C:12](=[O:16])[CH:13]=[CH:14][CH:15]=2)(=[O:9])=[O:8])[CH2:2][CH2:3][O:4][CH2:5][CH2:6]1

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 19883098HCID 19883098, compound

Product 1

HCID 19883096HCID 19883096, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
45 °C

Procedure

To a solution of 2-(morpholine-4-sulphonyl)-6-benzyloxypyridine (0.6 g) in acetic acid (10 cm3) was added 48% hydrobromic acid (10 cm3). The mixture was heated to 45° C., then stirred until the reaction was complete. The mixture was cooled, quenched in water (50 cm3) and the product extracted into ethyl acetate (4×20 cm3). The combined organic layers were washed with water, dried over anhydrous magnesium sulphate and the solvent evaporated under reduced pressure. The crude product was purified by silica chromatography eluting with hexane containing a gradually increased proportion of ethyl acetate (from 50%-60%).

Workup

  1. temperatureThe mixture was cooled
  2. customquenched in water (50 cm3)
  3. extractionthe product extracted into ethyl acetate (4×20 cm3)
  4. washThe combined organic layers were washed with water
  5. dry with materialdried over anhydrous magnesium sulphate
  6. customthe solvent evaporated under reduced pressure
  7. customThe crude product was purified by silica chromatography
  8. washeluting with hexane containing a gradually increased proportion of ethyl acetate (from 50%-60%)

Sources & evidence

ORD record
ord-8119af4ae97c42f98f80f4bd434372bb
Source dataset
uspto-grants-1992_08
Patent number
US05137886

Reaction notes

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