4-(Bromoacetyl)benzonitrile → 4-(2-Amino-1,3-thiazol-4-yl)benzonitrile

HRID 1191069Notes

Reaction equation

HRID 1191069 reaction equation
[C:1]([C:3]1[CH:12]=[CH:11][C:6]([C:7](=O)[CH2:8]Br)=[CH:5][CH:4]=1)#[N:2].[NH2:13][C:14]([NH2:16])=[S:15].C(=O)(O)[O-].[Na+]>C(O)C>[NH2:16][C:14]1[S:15][CH:8]=[C:7]([C:6]2[CH:11]=[CH:12][C:3]([C:1]#[N:2])=[CH:4][CH:5]=2)[N:13]=1

Participants

5

Reactant 3

HCID 986544-(Bromoacetyl)benzonitrileHCID 516892Sodium BicarbonateHCID 2723790Thiourea

Product 1

HCID 20495894-(2-Amino-1,3-thiazol-4-yl)benzonitrile

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Slurry 4-cyanophenacyl bromide (40 g, 179 mmol), thiourea (13.6 g, 181 mmol) and sodium bicarbonate (15.3 g, 181 mmol) in absolute ethanol (560 mL). Stir the mixture at reflux for 20 h under a nitrogen atmosphere. Cool the slurry to room temperature, filter, wash the solids with ethanol (100 mL), water (3×75 mL) and hexane (3×75 mL). Collect the yellow solid, add water (200 mL) and stir the slurry for 30 min at room temperate. Filter and wash the solid with hexane (excess). Slurry the solid in EtOAc (50 mL) and concentrate in vacuo twice to remove residual water. Collect the desired intermediate as a light yellow solid (36 g, 99%). MS (ES+) m/z: 202.1 (M+H)+.

Workup

  1. temperatureat reflux for 20 h under a nitrogen atmosphere
  2. filtrationfilter
  3. washwash the solids with ethanol (100 mL), water (3×75 mL) and hexane (3×75 mL)
  4. customCollect the yellow solid
  5. additionadd water (200 mL)
  6. stirringstir the slurry for 30 min at room temperate
  7. filtrationFilter
  8. washwash the solid with hexane (excess)
  9. concentrationconcentrate in vacuo twice
  10. customto remove residual water
  11. customCollect the desired intermediate as a light yellow solid (36 g, 99%)

Sources & evidence

ORD record
ord-06f2fc3fe8a7410d849a4c8fe73f0ea8
Source dataset
uspto-grants-2014_03
Patent number
US08680091B2

Reaction notes

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