N-bromobutanimide → 5-Bromo-2-ethoxy-1,3-thiazole

HRID 1958505Notes

Reaction equation

HRID 1958505 reaction equation
[CH:1]([O:4][C:5]1[S:6][CH:7]=[CH:8][N:9]=1)(C)[CH3:2].[Br:10]N1C(=O)CCC1=O.C(OCC)(=O)C.CCCCCC>CN(C=O)C>[Br:10][C:7]1[S:6][C:5]([O:4][CH2:1][CH3:2])=[N:9][CH:8]=1

Participants

5

Reactant 3

HCID 67184N-bromobutanimideHCID 21226206Ethyl acetate hexaneHCID 21334097HCID 21334097, compound

Product 1

HCID 457875615-Bromo-2-ethoxy-1,3-thiazoleYield 91.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-isopropoxythiazole (300 mg, 2.32 mmol) in DMF (2 mL) was added N-bromosuccinimide (620 mg, 3.48 mmol). The mixture was stirred at room temperature for 3 hours then subjected to flash column chromatography using 10% ethyl acetate/hexane to give a colorless oil (440 mg, 91% yield). LCMS (Conditions C): Tr 3.27 min.; (M+H): 207.88 (20%), 209.88 (20%), 179.87 (100%), 181.87 (100%).

Sources & evidence

ORD record
ord-1dc71ef0b31641ad85e606ee49e9f83d
Source dataset
uspto-grants-2013_04
Patent number
US08410128B2

Reaction notes

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