Hydrochloric Acid → HCID 135830963, compound

HRID 1824813Notes

Reaction equation

HRID 1824813 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:20]#[N:21])[C:6]2[S:10][C:9]([C:11]3[CH:16]=[CH:15][C:14]([O:17]C)=[CH:13][CH:12]=3)=[N:8][C:7]=2[CH:19]=1.Cl>B(Br)(Br)Br>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:20]#[N:21])[C:6]2[S:10][C:9]([C:11]3[CH:12]=[CH:13][C:14]([OH:17])=[CH:15][CH:16]=3)=[N:8][C:7]=2[CH:19]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 22144549HCID 22144549, compound

Product 1

HCID 135830963HCID 135830963, compoundYield 18.4%

Reagents, catalysts & solvents 1

HCID 25134Boron tribromideSolvent

Procedure

5-Methoxy-2-(4-methoxy-phenyl)-benzothiazole-7-carbonitrile (0.04 g, 0.135 mmol) was suspended in boron tribromide (1M in methylene chloride, 5.0 mL) and stirred at room temp under nitrogen for 48 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 NaHCO3, 3) saturated brine and concentrated in vacuo. This material was further purified by chromatography on silica yielding the title compound (14 mg, 39%) as a tan solid. Mass spec: MH+=296 5-Methoxy-2-(4-hydroxy-phenyl)-benzothiazole-7-carbonitrile (7 mg, 18%) was also obtained as a white solid from this chromatography. The starting 7-Cyano-5-Methoxy-2-(4-methoxy-phenyl)-benzothiazole was prepared as follows:

Workup

  1. customReaction
  2. extractionextracted with ethyl acetate
  3. washEthyl acetate extracts were washed with: 1) hydrochloric acid (1.0M), 2) saturated NaHCO3, 3) saturated brine
  4. concentrationconcentrated in vacuo
  5. customThis material was further purified by chromatography on silica yielding the title compound (14 mg, 39%) as a tan solid

Sources & evidence

ORD record
ord-4961330331ba480994d473598fa42dec
Source dataset
uspto-grants-2006_05
Patent number
US07045539B2

Reaction notes

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