Ethyl Acetate → Ethyl {2-[4-(3-chloropropoxy)phenyl]-4-methyl-1,3-thiazol-5-yl}acetate

HRID 1710793Notes

Reaction equation

HRID 1710793 reaction equation
Br[CH:2]([C:9](=O)[CH3:10])[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].[Cl:12][CH2:13][CH2:14][CH2:15][O:16][C:17]1[CH:22]=[CH:21][C:20]([C:23](=[S:25])[NH2:24])=[CH:19][CH:18]=1.C(OCC)(=O)C>CN(C)C=O>[Cl:12][CH2:13][CH2:14][CH2:15][O:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[S:25][C:2]([CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5])=[C:9]([CH3:10])[N:24]=2)=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 12933940Ethyl 3-bromo-4-oxopentanoateHCID 594574624-(3-Chloropropoxy)benzenecarbothioamide

Product 1

HCID 59457484Ethyl {2-[4-(3-chloropropoxy)phenyl]-4-methyl-1,3-thiazol-5-yl}acetateYield 40%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of ethyl 3-bromo-4-oxopentanoate (2 g, 8.98 mmol, 1 eq), and 4-(3-chloropropoxy)benzenecarbothioamide ax71 (2.06 g, 8.97 mmol, 1 eq) in dimethylformamide (4 ml) is stirred at 100° C. for 2 h. The reaction mixture is then added to ethyl acetate (200 ml) and the precipitate filtered off. The organic layer is washed with water (4×100 ml), brine, dried over magnesium sulfate and filtered. The solvent is removed under reduced pressure. Purification by chromatography over silicagel (eluent: benzine/ethyl acetate 95:5 to 85:15) affords 1.3 g of ethyl {2-[4-(3-chloropropoxy)phenyl]-4-methyl-1,3-thiazol-5-yl}acetate i102.

Workup

  1. filtrationthe precipitate filtered off
  2. washThe organic layer is washed with water (4×100 ml), brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customThe solvent is removed under reduced pressure
  6. customPurification by chromatography over silicagel (eluent: benzine/ethyl acetate 95:5 to 85:15)

Sources & evidence

ORD record
ord-d824e8f743c74c1ca0d386bfafd099cc
Source dataset
uspto-grants-2010_09
Patent number
US07790720B2

Reaction notes

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