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

HRID 1744916Notes

Reaction equation

HRID 1744916 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 fitered. 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. washIt was washed well with water
  6. customdried

Sources & evidence

ORD record
ord-63045a7327d34c5ca9b00b633ef3bf54
Source dataset
uspto-grants-2006_03
Patent number
US07018997B2

Reaction notes

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