N-bromobutanimide → N-(3-((5-bromothiazol-2-yl)amino)phenyl)methanesulfonamide

HRID 1035832Notes

Reaction equation

HRID 1035832 reaction equation
[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[NH:6][C:7]1[CH:8]=[C:9]([NH:13][S:14]([CH3:17])(=[O:16])=[O:15])[CH:10]=[CH:11][CH:12]=1.[Br:18]N1C(=O)CCC1=O>C1COCC1.CCCCCC>[Br:18][C:5]1[S:1][C:2]([NH:6][C:7]2[CH:8]=[C:9]([NH:13][S:14]([CH3:17])(=[O:16])=[O:15])[CH:10]=[CH:11][CH:12]=2)=[N:3][CH:4]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 86674184N-(3-(thiazol-2-ylamino)phenyl)methanesulfonamide

Product 1

HCID 86674186N-(3-((5-bromothiazol-2-yl)amino)phenyl)methanesulfonamideYield 86%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

To a stirred solution of N-(3-(thiazol-2-ylamino)phenyl)methanesulfonamide 55 (1.17 g, 1.85 mmol) in anhydrous THF (25 mL) was added N-bromosuccinimide (0.363 g, 2.03 mmol) at room temperature. Reaction mixture was stirred for 14 hours at ambient temperature. After completion of the reaction (as judged by TLC), it was concentrated and the crude product was MPLC (Biotage) silica column chromatographed using Acetone:Hexane as an eluent to obtain N-(3-((5-bromothiazol-2-yl)amino)phenyl)methanesulfonamide 56 (0.55 g, 86% yield). MS (ES) m/z 348 (M+H+).

Workup

  1. customReaction mixture
  2. customAfter completion of the reaction (as judged by TLC), it
  3. concentrationwas concentrated
  4. customchromatographed

Sources & evidence

ORD record
ord-b02677fdde1240e18eddf30d49e08958
Source dataset
uspto-grants-2013_10
Patent number
US08546400B2

Reaction notes

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