Hydrogen Bromide → HCID 66753136, compound

HRID 1642386Notes

Reaction equation

HRID 1642386 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:14](=[O:15])[N:13]3[CH:16]=[CH:17][S:18][C:12]3=[N:11][C:10]=2[CH3:19])=[CH:5][CH:4]=1.Br>C(O)(=O)C>[OH:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[C:14](=[O:15])[N:13]3[CH:16]=[CH:17][S:18][C:12]3=[N:11][C:10]=2[CH3:19])=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 66752909HCID 66752909, compound

Product 1

HCID 66753136HCID 66753136, compoundYield 65.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Intermediate 9 (4.8 g, 17.726 mmol) was treated with HBr (35 ml) and acetic acid (35 ml) at room temperature and the reaction mixture was then heated to reflux overnight for 15.0 g. After completion of the reaction, the mixture was concentrated and basified with NaHCO3 and extracted with ethyl acetate. Combined organic layer was washed with water, brine, dried over anhydrous Na2SO4 purified using 5% CH3OH in chloroform to afford 3.0 g of the desired compound; 1H NMR (300 MHz, DMSO-d6) δ 2.17 (s, 3H), 6.76-6.79 (m, 2H), 7.05-7.08 (m, 2H), 7.48 (d, J=4.8 Hz, 1H), 7.96 (d, J=5.1 Hz, 1H), 9.47 (s, 1H); ESI-MS (m/z) 259.50 (M+H)+.

Workup

  1. temperaturethe reaction mixture was then heated
  2. temperatureto reflux overnight for 15.0 g
  3. customAfter completion of the reaction
  4. concentrationthe mixture was concentrated
  5. extractionextracted with ethyl acetate
  6. washCombined organic layer was washed with water, brine
  7. dry with materialdried over anhydrous Na2SO4
  8. custompurified

Sources & evidence

ORD record
ord-e20c2d74b3aa4b24ac45bf733827f8e0
Source dataset
uspto-grants-2012_02
Patent number
US08119647B2

Reaction notes

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