Dimethylformamide → 5-Bromo-2-(1-methyl-1H-1,2,4-triazol-5-yl)thiazole

HRID 1660737Notes

Reaction equation

HRID 1660737 reaction equation
[CH3:1][N:2]1[C:6]([C:7]2[S:8][CH:9]=[CH:10][N:11]=2)=[N:5][CH:4]=[N:3]1.CN(C)C=O.[Br:17]N1C(=O)CCC1=O>O>[Br:17][C:9]1[S:8][C:7]([C:6]2[N:2]([CH3:1])[N:3]=[CH:4][N:5]=2)=[N:11][CH:10]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 67184N-bromobutanimideHCID 67428280methyl-5-thiazol-2-yl-1H-[1,2,4]triazole

Product 1

HCID 534011685-Bromo-2-(1-methyl-1H-1,2,4-triazol-5-yl)thiazoleYield 969%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
22 °C

Procedure

To a mixture of methyl-5-thiazol-2-yl-1H-[1,2,4]triazole (6.55 g; 39 4 mmol) and dimethylformamide (32 mL), add N-bromosuccinimide (14 g, 78.8 mmol) in three portions over 1 h. Stir the mixture at 22° C. for 18 h and then add to water (300 mL) chilled to 0-5° C. Separate the aqueous layer and extract with methyl-t-butyl ether (2×200 mL). Combine the organic layers and wash with 7% aqueous sodium hydrogen carbonate (100 mL) and then dry over sodium sulfate. Filter and evaporate the solvent to afford the title compound (9.5 g, 93%). ES/MS m/z (79Br/81Br) 245/247 (M+1)+.

Workup

  1. temperaturechilled to 0-5° C
  2. customSeparate the aqueous layer
  3. extractionextract with methyl-t-butyl ether (2×200 mL)
  4. washCombine the organic layers and wash with 7% aqueous sodium hydrogen carbonate (100 mL)
  5. dry with materialdry over sodium sulfate
  6. filtrationFilter
  7. customevaporate the solvent

Sources & evidence

ORD record
ord-3e53e45569fc4a1888acbe7353c59e42
Source dataset
uspto-grants-2011_10
Patent number
US08030304B2

Reaction notes

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