Hydrogen Bromide → HCID 68980802, compound

HRID 1820838Notes

Reaction equation

HRID 1820838 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([C:13]1[N:14]=[C:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[S:16][CH:17]=1)[CH:7]=[CH:6]2.Br>CC(O)=O>[C:18]1([C:15]2[S:16][CH:17]=[C:13]([C:8]3[CH:9]=[C:10]4[C:5](=[CH:6][CH:7]=3)[CH:4]=[C:3]([OH:2])[CH:12]=[CH:11]4)[N:14]=2)[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 68984203HCID 68984203, compound

Product 1

HCID 68980802HCID 68980802, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 4-(6-methoxy-2-naphthyl)-2-phenyl-1,3-thiazole (804 mg, 2.53 mmol), prepared in the previous step, in 50 mL of glacial HOAc plus 25 mL of 48% HBr was stirred under nitrogen at 120° C. for 3 h. The solvent was removed under reduced pressure and the residue partitioned between 10% methanol-methylene chloride and 5% NaHCO3. (Note: The solid that did not dissolve in either layer was collected by filtration and saved as the HCL salt of the desired product). The aqueous layer was separated and extracted three times with 10% methanol-methylene chloride. The combined extracts were dried (MgSO4), filtered and the solvent removed under reduced pressure to give 6-(2-phenyl-1,3-thiazol-4-yl)-2-naphthol (650 mg, 85%) as a brown solid, mp 194-197° C. Elemental Analysis for C19H13NOS Calc'd: C, 75.22; H, 4.32; N, 4.62. Found: C, 74.22; H, 4.12; N, 4.43

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue partitioned between 10% methanol-methylene chloride and 5% NaHCO3
  3. dissolution(Note: The solid that did not dissolve in either layer
  4. filtrationwas collected by filtration
  5. customThe aqueous layer was separated
  6. extractionextracted three times with 10% methanol-methylene chloride
  7. dry with materialThe combined extracts were dried (MgSO4)
  8. filtrationfiltered
  9. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-a7175105b8a64d83a77954229cfb2a75
Source dataset
uspto-grants-2009_10
Patent number
US07605172B2

Reaction notes

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