Bromobenzyl Cyanide → N-(4-amino-5-phenyl-thiazol-2-yl)-acetamide

HRID 1639522Notes

Reaction equation

HRID 1639522 reaction equation
Br[CH:2]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[C:3]#[N:4].[C:11]([NH:14][C:15]([NH2:17])=[S:16])(=[O:13])[CH3:12]>C(O)C>[C:11]([NH:14][C:15]1[S:16][C:2]([C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)=[C:3]([NH2:4])[N:17]=1)(=[O:13])[CH3:12]

Participants

4

Reactant 2

HCID 22044Bromobenzyl CyanideHCID 2723593Acetylthiourea

Product 1

HCID 85841531N-(4-amino-5-phenyl-thiazol-2-yl)-acetamideYield 23.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

α-Bromophenylacetonitrile (1.08 g, 5.48 mmol) in ethanol (10 ml) was treated with N-acetylthiourea (649 mg, 5.49 mmol) at ambient temperature for 4 hr, and then heated to reflux for 3.5 hr. The cooled mixture was concentrated in vacuo and then partitioned between dichloromethane and saturated aqueous sodium bicarbonate. The organic phase was washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo. Flash chromatography on silica gel (ethyl acetate/hexanes) yielded 2-(acetylamino)-4-amino-5-phenylthiazole (295 mg, 23%).

Workup

  1. temperatureheated
  2. temperatureto reflux for 3.5 hr
  3. concentrationThe cooled mixture was concentrated in vacuo
  4. custompartitioned between dichloromethane and saturated aqueous sodium bicarbonate
  5. washThe organic phase was washed with brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d7ddcf975d934cd196baeb7fb4c03fd9
Source dataset
uspto-grants-2012_02
Patent number
US08110568B2

Reaction notes

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