Hydrogen Bromide → HCID 178515901, compound

HRID 1722006Notes

Reaction equation

HRID 1722006 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:10]2[NH:11][CH:12]=[C:13]([C:15]3[S:16][CH:17]=[CH:18][CH:19]=3)[N:14]=2)[CH:5]=[CH:6][C:7]=1[O:8]C.Br>CC(O)=O>[Br:1][C:2]1[CH:3]=[C:4]([C:10]2[NH:11][CH:12]=[C:13]([C:15]3[S:16][CH:17]=[CH:18][CH:19]=3)[N:14]=2)[CH:5]=[CH:6][C:7]=1[OH:8]

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 178488930HCID 178488930, compound

Product 1

HCID 178515901HCID 178515901, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 32 (5.7 g, 0.017 mole), glacial HOAc (30 ml), and 48% HBr (85 ml) was stirred and heated at reflux for 12 hours. The hydrobromide salt that precipitated on cooling was collected and shown to consist of a mixture of 32 and 33. The mixture was resuspended in glacial HOAc (30 ml)-48% HBr (85 ml) and again heated at reflux for 12 hours. The precipitated hydrobromide was collected, washed with HOAc and Et2O and then stirred with saturated NaHCO3 (100 ml) for 2 days. The solid was collected, chromatographed on silica gel and the product eluted with 70 toluene--30 EtOAc to yield 1.2 g (22%) of 33, m.p. 125°-130° C.

Workup

  1. temperatureheated
  2. temperatureat reflux for 12 hours
  3. customThe hydrobromide salt that precipitated
  4. temperatureon cooling
  5. customwas collected
  6. additionto consist of a mixture of 32 and 33
  7. temperatureagain heated
  8. temperatureat reflux for 12 hours
  9. customThe precipitated hydrobromide was collected
  10. washwashed with HOAc and Et2O
  11. stirringstirred with saturated NaHCO3 (100 ml) for 2 days
  12. customThe solid was collected
  13. customchromatographed on silica gel
  14. washthe product eluted with 70 toluene

Sources & evidence

ORD record
ord-3c8be11802fb47b393528c038d391cbb
Source dataset
uspto-grants-1989_08
Patent number
US04853383

Reaction notes

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