Hydrochloric Acid → HCID 135830949, compound

HRID 1824810Notes

Reaction equation

HRID 1824810 reaction equation
[I:1][C:2]1[C:7]2[N:8]=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([O:17]C)=[CH:13][CH:12]=3)[S:10][C:6]=2[CH:5]=[C:4]([O:19]C)[CH:3]=1.Cl>B(Br)(Br)Br>[I:1][C:2]1[C:7]2[N:8]=[C:9]([C:11]3[CH:12]=[CH:13][C:14]([OH:17])=[CH:15][CH:16]=3)[S:10][C:6]=2[CH:5]=[C:4]([OH:19])[CH:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 22144518HCID 22144518, compound

Product 1

HCID 135830949HCID 135830949, compound

Reagents, catalysts & solvents 1

HCID 25134Boron tribromideSolvent

Procedure

4-Iodo-6-methoxy-2-(4-Methoxy-phenyl)-benzothiazole (175 mg, 0.44 mmol) [Compound of Example 1d] was suspended in boron tribromide (1M in methylene chloride, 3.5 mL) and stirred at room temp under nitrogen for 72.0 hr. Reaction was poured into aqueous hydrochloric acid (1M) and extracted with ethyl acetate. Ethyl acetate extracts were washed with: 1) hydrochloric acid (1.0M), 2) saturated brine and concentrated in vacuo. Washed solid was further purified by flash chromatography on silica affording the title compound (158 mg, 97%) as a yellow solid. MH+=370

Workup

  1. customReaction
  2. extractionextracted with ethyl acetate
  3. washEthyl acetate extracts were washed with: 1) hydrochloric acid (1.0M), 2) saturated brine
  4. concentrationconcentrated in vacuo
  5. washWashed solid
  6. customwas further purified by flash chromatography on silica affording the title compound (158 mg, 97%) as a yellow solid

Sources & evidence

ORD record
ord-09a88e49ff984f8e8a163869049404a7
Source dataset
uspto-grants-2006_05
Patent number
US07045539B2

Reaction notes

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