Hydrochloric Acid → HCID 135830968, compound

HRID 1824809Notes

Reaction equation

HRID 1824809 reaction equation
[Br: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>[Br: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 22144553HCID 22144553, compound

Product 1

HCID 135830968HCID 135830968, compound

Reagents, catalysts & solvents 1

HCID 25134Boron tribromideSolvent

Procedure

4-Bromo-6-methoxy-2-(4-Methoxy-phenyl)-benzothiazole (200 mg, 0.57 mmol) was suspended in boron tribromide (1M in methylene chloride, 7.5 mL) and stirred at room temp under nitrogen for 3.0 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 (184 mg, 100%) as a yellow solid. MH+=322

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 (184 mg, 100%) as a yellow solid

Sources & evidence

ORD record
ord-93bcb7867a2a4a93bbc8795ab8cc3839
Source dataset
uspto-grants-2006_05
Patent number
US07045539B2

Reaction notes

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