4-Bromophenacyl bromide → HCID 1130426, compound

HRID 589585Notes

Reaction equation

HRID 589585 reaction equation
[CH3:1][CH2:2][CH2:3][C:4]1[CH:5]=[C:6]([C:10]([NH2:12])=[S:11])[CH:7]=[CH:8][N:9]=1.[Br:13][C:14]1[CH:23]=[CH:22][C:17]([C:18](=O)[CH2:19]Br)=[CH:16][CH:15]=1>CCO>[Br:13][C:14]1[CH:23]=[CH:22][C:17]([C:18]2[N:12]=[C:10]([C:6]3[CH:7]=[CH:8][N:9]=[C:4]([CH2:3][CH2:2][CH3:1])[CH:5]=3)[S:11][CH:19]=2)=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 74544-Bromophenacyl bromideHCID 666418Prothionamide

Product 1

HCID 1130426HCID 1130426, compoundYield 79.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

As shown in FIG. 27, in reaction (a) a mixture of prothionamide (9.01 g, 50.0 mmol) and 4-bromophenacyl bromide 6a (13.9 g, 50.0 mmol) in EtOH (400 mL) was stirred at 70° C. for 1 h. After cooled to room temperature, the precipitation was filtered off with EtOAc and washed with EtOAc and saturated aqueous NaHCO3. The organic layer was washed with brine, dried over Na2SO4, and concentrated to give 4-(4-bromophenyl)-2-(2-propylpyridin-4-yl)thiazole 2 (14.3 g, 79%) as a light-yellow solid.

Workup

  1. temperatureAfter cooled to room temperature
  2. customthe precipitation
  3. filtrationwas filtered off with EtOAc
  4. washwashed with EtOAc and saturated aqueous NaHCO3
  5. washThe organic layer was washed with brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-b7cc05f5c7c746799f687a19df765441
Source dataset
uspto-grants-2016_01
Patent number
US09233941B2

Reaction notes

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