Hydrochloric Acid → HCID 135830967, compound

HRID 1824811Notes

Reaction equation

HRID 1824811 reaction equation
[Cl: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>[Cl: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 22144555HCID 22144555, compound

Product 1

HCID 135830967HCID 135830967, compoundYield 98.2%

Reagents, catalysts & solvents 1

HCID 25134Boron tribromideSolvent

Procedure

4-Chloro-6-methoxy-2-(4-Methoxy-phenyl)-benzothiazole (0.27 g, 0.88 mmol) was suspended in boron tribromide (1M in methylene chloride, 7.0 mL) and stirred at room temp under nitrogen for 18.0 hr. Reaction was poured cautiously into aqueous 1M hydrochloric acid and extracted with ethyl acetate. Ethyl acetate extracts were washed with: 1) hydrochloric acid (1.0M), 2) saturated brine and concentrated in vacuo. Solid was washed with methylene chloride/methanol (97:3, 10 mL), and dried under vacuum yielding the title compound (0.240 g, 98%) as a tan solid. Mass spec: MH+=278 The starting 4-Chloro-6-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 brine
  4. concentrationconcentrated in vacuo
  5. washSolid was washed with methylene chloride/methanol (97:3, 10 mL)
  6. customdried under vacuum

Sources & evidence

ORD record
ord-2ddc04543a7149a7835635a0cc7a4d76
Source dataset
uspto-grants-2006_05
Patent number
US07045539B2

Reaction notes

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