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

HRID 80221

Reaction equation

HRID 80221 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-71203114ad6d41cfaacd277bb5ec8620
Source dataset
uspto-grants-2014_09
Patent number
USRE045173E1

Linked notes

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