Ethyl orthoformate → 6-Bromo-1,3-benzothiazole

HRID 2077618Notes

Reaction equation

HRID 2077618 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][C:3]=1[SH:9].[CH:10](OCC)(OCC)OCC>>[Br:8][C:5]1[CH:6]=[CH:7][C:2]2[N:1]=[CH:10][S:9][C:3]=2[CH:4]=1

Participants

3

Reactant 2

HCID 31214Ethyl orthoformateHCID 12090452-Amino-5-bromobenzene-1-thiol

Product 1

HCID 27951716-Bromo-1,3-benzothiazole

Procedure

A 100 mL, one neck round bottom flask was charged with 2-amino-5-bromobenzenethiol (1.19 g, 5.83 mmol), triethyl orthoformate (9.70 ml, 58.3 mmol), 10 mL TFE, and a stirbar. A reflux condenser with a vacuum/nitrogen inlet was a fixed to the flask, and the system was degassed by evacuating to 5 mm Hg, and refilling with nitrogen. To the solution was added 200 mg dithiothreitol, and the reaction was heated using a 80° C. oil bath for 12 h. The reaction was cooled, and concentrated in vacuo. The crude was not characterized further.

Workup

  1. customA reflux condenser with a vacuum/nitrogen inlet was
  2. customthe system was degassed
  3. customby evacuating to 5 mm Hg
  4. additionTo the solution was added 200 mg dithiothreitol
  5. temperaturethe reaction was heated
  6. customusing a 80° C.
  7. customfor 12 h
  8. temperatureThe reaction was cooled
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-453aeb3fb75142ad8beec937bc1bdd21
Source dataset
uspto-grants-2011_04
Patent number
US07928140B2

Reaction notes

Loading…