HCID 178418963, compound → Ethyl 6-bromo-2-benzothiazoleacetate

HRID 424944Notes

Reaction equation

HRID 424944 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[S:7][C:8]2[CH:16]=[C:15]([Br:17])[CH:14]=[CH:13][C:9]=2[NH:10][C:11]=1O)=[O:5])[CH3:2]>C(O)(=O)C.[Zn]>[CH2:1]([O:3][C:4](=[O:5])[CH2:6][C:11]1[S:7][C:8]2[CH:16]=[C:15]([Br:17])[CH:14]=[CH:13][C:9]=2[N:10]=1)[CH3:2]

Participants

4

Reactant 1

HCID 178418963HCID 178418963, compound

Product 1

HCID 21041509Ethyl 6-bromo-2-benzothiazoleacetate

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
110 °C

Procedure

7-Bromo-3-hydroxy-4H-benzo[1,4]thiazine-2-carboxylic acid ethyl ester (2.47 g, 7.8 mmol) was dissolved in 50 mL of acetic acid and heated to 110° C. under nitrogen. Zinc powder (7.5 g, 114.7 mmol) was added in portions at room temperature over 80 minutes. The mixture was stirred at 110° C. for additional 2 hours and cooled to room temperature. Zinc was filtered off and rinsed with 20 mL EtOAc. The combined filtrate was concentrated to yellow crystals and purified by column chromatography (silica gel, 20:90 EtOAc:hexane) to give (6-bromo-benzothiazol-2-yl)-acetic acid ethyl ester.

Workup

  1. temperaturecooled to room temperature
  2. filtrationZinc was filtered off
  3. washrinsed with 20 mL EtOAc
  4. concentrationThe combined filtrate was concentrated to yellow crystals
  5. custompurified by column chromatography (silica gel, 20:90 EtOAc:hexane)

Sources & evidence

ORD record
ord-8bd730fc59884e80bdaad0ef9f602698
Source dataset
uspto-grants-2012_01
Patent number
US08106088B2

Reaction notes

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