N-bromobutanimide → HCID 59187443, compound

HRID 1944502Notes

Reaction equation

HRID 1944502 reaction equation
[Br:1]N1C(=O)CCC1=O.[Cl:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[C:16]1[S:20][C:19]([CH3:21])=[N:18][CH:17]=1>C(Cl)(Cl)(Cl)Cl.C(Cl)Cl>[Br:1][CH2:21][C:19]1[S:20][C:16]([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[Cl:9])=[CH:17][N:18]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 59187446HCID 59187446, compound

Product 1

HCID 59187443HCID 59187443, compound

Reagents, catalysts & solvents 2

HCID 5943Carbon TetrachlorideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
75 °C

Procedure

N-Bromosuccinimide (344 mg, 1.61 mmol) is added to a solution of 5-(2-chlorophenyl)-2-methylthiazole (337 mg, 1.93 mmol) in carbon tetrachloride (15 mL). The above solution is stirred at 75° C. for 18 h. The solution is diluted with CH2Cl2 (50 mL) and washed with saturated NaHCO3 (50 mL) and brine (30 mL). The organic layer is dried (MgSO4), filtered, concentrated and purified by silica gel chromatography (EtOAc/hexane, gradient) to give 2-(bromomethyl)-5-(2-chlorophenyl)thiazole 7 as a white solid. MS calcd. for C10H8BrClNS (M+H+) 287.9. found 286.9.

Workup

  1. washwashed with saturated NaHCO3 (50 mL) and brine (30 mL)
  2. dry with materialThe organic layer is dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. custompurified by silica gel chromatography (EtOAc/hexane, gradient)

Sources & evidence

ORD record
ord-1e2abb98b6f9457e8c44793136e290e9
Source dataset
uspto-grants-2013_03
Patent number
US08394841B2

Reaction notes

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