Ethyl Acetate → 1-(Benzothiazol-6-ylamino)-butan-2-one

HRID 2383907

Reaction equation

HRID 2383907 reaction equation
C([O-])(=O)C.[Na+].Br[CH2:7][C:8](=[O:11])[CH2:9][CH3:10].[S:12]1[C:16]2[CH:17]=[C:18]([NH2:21])[CH:19]=[CH:20][C:15]=2[N:14]=[CH:13]1.C(OCC)(=O)C>CO.CCCCCC>[S:12]1[C:16]2[CH:17]=[C:18]([NH:21][CH2:7][C:8](=[O:11])[CH2:9][CH3:10])[CH:19]=[CH:20][C:15]=2[N:14]=[CH:13]1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 131561-Bromo-2-butanoneHCID 682886-AminobenzothiazoleHCID 517045Sodium Acetate

Product 1

HCID 596361951-(Benzothiazol-6-ylamino)-butan-2-oneYield 34.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8058HexaneSolvent

Procedure

Sodium acetate (300 mg, 3.66 mmol) and 1-bromo-butan-2-one (0.373 mL, 3.66 mmol) were added to a stirred solution of benzothiazol-6-ylamine (500 mg, 3.328 mmol) in methanol (10 mL) under nitrogen atmosphere. The resulting reaction mass was stirred at room temperature for 24 hours. The reaction was monitored by TLC (20% ethyl acetate in hexane). The reaction mixture was filtered and the solid collected was dried under reduced pressure to afford 250 mg of the product (32% yield).

Workup

  1. customThe resulting reaction mass
  2. filtrationThe reaction mixture was filtered
  3. customthe solid collected
  4. customwas dried under reduced pressure

Sources & evidence

ORD record
ord-7adb840d11424fd2a79c0e22e8c79c41
Source dataset
uspto-grants-2012_09
Patent number
US08263635B2

Linked notes

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