Hydrogen Bromide → HCID 68982787, compound

HRID 1820846Notes

Reaction equation

HRID 1820846 reaction equation
[Cl:1][C:2]1[CH:25]=[CH:24][CH:23]=[C:22]([Cl:26])[C:3]=1[CH2:4][C:5]1[S:6][CH:7]=[C:8]([C:10]2[CH:19]=[CH:18][C:17]3[C:12](=[CH:13][CH:14]=[C:15]([O:20]C)[CH:16]=3)[CH:11]=2)[N:9]=1.Br>CC(O)=O>[Cl:26][C:22]1[CH:23]=[CH:24][CH:25]=[C:2]([Cl:1])[C:3]=1[CH2:4][C:5]1[S:6][CH:7]=[C:8]([C:10]2[CH:11]=[C:12]3[C:17](=[CH:18][CH:19]=2)[CH:16]=[C:15]([OH:20])[CH:14]=[CH:13]3)[N:9]=1

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 68979890HCID 68979890, compound

Product 1

HCID 68982787HCID 68982787, compoundYield 80.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 2-(2,6-dichlorobenzyl)-4-(6-methoxy-2-naphthyl)-1,3-thiazole (390 mg, 0.975 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 3.5 h and then stood overnight at room temperature. The reaction was concentrated under reduced pressure. The residue was dissolved in 20% methanol-methylene chloride and neutralized with the addition of an excess of 5% NaHCO3. The aqueous layer was separated and extracted three times with 20% methanol-methylene chloride. The combined extracts were dried (MgSO4), filtered and the solvent removed under reduced pressure to give 6-[2-(2,6-dichlorobenzyl)-1,3-thiazol-4-yl]-2-naphthol (303 mg, 80%) as a brown solid, mp 191-193° C. Elemental Analysis for C20H13Cl2NOS Calc'd: C, 62.19; H, 3.39; N, 3.63. Found: C, 61.31; H, 3.30; N, 3.42.

Workup

  1. concentrationThe reaction was concentrated under reduced pressure
  2. dissolutionThe residue was dissolved in 20% methanol-methylene chloride
  3. additionneutralized with the addition of an excess of 5% NaHCO3
  4. customThe aqueous layer was separated
  5. extractionextracted three times with 20% methanol-methylene chloride
  6. dry with materialThe combined extracts were dried (MgSO4)
  7. filtrationfiltered
  8. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-fddfb0b65d2245678e15e7a6b1fa6d71
Source dataset
uspto-grants-2009_10
Patent number
US07605172B2

Reaction notes

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