Benzo(d)thiazol-2-amine → ethyl imidazo[2,1-b][1,3]benzothiazole-2-carboxylate

HRID 638836Notes

Reaction equation

HRID 638836 reaction equation
Br[CH2:2][C:3](=O)[C:4]([O:6][CH2:7][CH3:8])=[O:5].[NH2:10][C:11]1[S:12][C:13]2[CH:19]=[CH:18][CH:17]=[CH:16][C:14]=2[N:15]=1>CN(C=O)C>[N:10]1[C:3]([C:4]([O:6][CH2:7][CH3:8])=[O:5])=[CH:2][N:15]2[C:14]3[CH:16]=[CH:17][CH:18]=[CH:19][C:13]=3[S:12][C:11]=12

Participants

4

Reactant 2

HCID 8706Benzo(d)thiazol-2-amineHCID 66144Ethyl bromopyruvate

Product 1

HCID 1480574ethyl imidazo[2,1-b][1,3]benzothiazole-2-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Ethyl bromopyruvate (9.8 g, 50 mmol) was added dropwise to a stirred solution of 2-aminobenzothiazole (7.5 g, 50 mmol) in DMF (100 ml) at room temperature. After the addition, the reaction mixture was heated to reflux for 6 h. The reaction mixture was cooled to room temperature and quenched with ice cold water. The aqueous layer was neutralized with NH4OH and the separated solid was filtered. It was washed well with water and dried. The crude product obtained was taken to next step without purification.

Workup

  1. additionAfter the addition
  2. temperaturethe reaction mixture was heated
  3. temperatureto reflux for 6 h
  4. customquenched with ice cold water
  5. filtrationthe separated solid was filtered
  6. washIt was washed well with water
  7. customdried

Sources & evidence

ORD record
ord-826f3b8e42574ee88dab8d45fe1c9626
Source dataset
uspto-grants-2010_04
Patent number
US07691842B2

Reaction notes

Loading…