N-bromobutanimide → HCID 59402828, compound

HRID 875018Notes

Reaction equation

HRID 875018 reaction equation
[Br:1]N1C(=O)CCC1=O.[F:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[N:17]=[C:18]([CH3:21])[S:19][CH:20]=2)=[CH:12][CH:11]=1>C(Cl)(Cl)(Cl)Cl.C(Cl)Cl>[Br:1][CH2:21][C:18]1[S:19][CH:20]=[C:16]([C:13]2[CH:12]=[CH:11][C:10]([F:9])=[CH:15][CH:14]=2)[N:17]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 7318944-(4-Fluorophenyl)-2-methylthiazole

Product 1

HCID 59402828HCID 59402828, compoundYield 101.3%

Reagents, catalysts & solvents 2

HCID 5943Carbon TetrachlorideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
80 °C

Procedure

N-Bromosuccinimide (3.22 g, 18.13 mmol) was added to a solution of 4-(4-fluorophenyl)-2-methylthiazole (3.5 g, 18.13 mmol) in CCl4 (30.0 mL) and the reaction was refluxed at 80° C. overnight. The reaction mixture was then diluted with CH2Cl2, washed with water and brine, dried over anhydrous Na2SO4, and concentrated under reduced pressure to yield crude 2-(bromomethyl)-4-(4-fluorophenyl)thiazole (5 g), which was carried through without further purification. 1H NMR (400 MHz, DMSO) δ 8.18 (s, 1H), 7.93-8.01 (m, 2H), 7.26-7.31 (m, 2H), 5.07 (s, 2H). MS (ESI) m/z: Calculated for C10H7BrFNS: 272.94. found: 273.9 (M+H)+

Workup

  1. washwashed with water and brine
  2. dry with materialdried over anhydrous Na2SO4
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-fbd4bc83f5ae46af88fa26a0dcf31690
Source dataset
uspto-grants-2015_03
Patent number
US08981084B2

Reaction notes

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