N-bromobutanimide → HCID 58207875, compound

HRID 1958503Notes

Reaction equation

HRID 1958503 reaction equation
[CH:1]([S:4][C:5]1[S:6][CH:7]=[CH:8][N:9]=1)([CH3:3])[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]([S:4][CH:1]([CH3:3])[CH3:2])=[N:9][CH:8]=1

Participants

5

Reactant 3

HCID 67184N-bromobutanimideHCID 12457581HCID 12457581, compoundHCID 21226206Ethyl acetate hexane

Product 1

HCID 58207875HCID 58207875, compoundYield 100.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-(isopropylthio)thiazole (260 mg, 1.63 mmol) in DMF (2 mL) was added N-bromosuccinimide (435.8 mg, 2.45 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 yellow oil (390 mg, 100% yield). LCMS (Conditions C): Tr 3.67 min.; (M+H): 237.86 (30%), 239.86 (30%), 195.86 (100%), 197.86 (100%).

Sources & evidence

ORD record
ord-f60a20baf12940beb46d047a33fbb0e2
Source dataset
uspto-grants-2013_04
Patent number
US08410128B2

Reaction notes

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