4-(Bromoacetyl)benzonitrile → HCID 17446227, compound

HRID 1190948Notes

Reaction equation

HRID 1190948 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].[CH3:13][NH:14][C:15]([NH2:17])=[S:16].C(=O)(O)[O-].[Na+]>C(O)C>[CH3:13][NH:14][C:15]1[S:16][CH:8]=[C:7]([C:6]2[CH:11]=[CH:12][C:3]([C:1]#[N:2])=[CH:4][CH:5]=2)[N:17]=1

Participants

5

Reactant 3

HCID 986544-(Bromoacetyl)benzonitrileHCID 516892Sodium BicarbonateHCID 2723704Methylthiourea

Product 1

HCID 17446227HCID 17446227, compoundYield 102.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
40 °C

Procedure

Slurry 4-cyanophenacyl bromide (1.12 g, 5 mmol) in absolute ethanol (25 mL). Heat to 40° C. to dissolve, then add N-methyl-thiourea (0.45 g, 5 mmol) and sodium bicarbonate (0.42 g, 5 mmol), and heat to reflux for 5 h. Cool to room temperature, filter the resulting off-white solid and wash with hexane (10 mL). Partition aqueous/ethanolic filtrate between water/EtOAc (4:1) and extract aqueous phase with EtOAc (2×25 mL). Dry the combined organic extracts over Na2SO4, concentrate in vacuo and combine with filtered solid from crude reaction mixture to obtain the desired intermediate (1.1 g, 99%) as an off-white solid suitable for use without additional purification. MS (ES+) m/z: 216 (M+H)+.

Workup

  1. dissolutionto dissolve
  2. temperatureto reflux for 5 h
  3. temperatureCool to room temperature
  4. filtrationfilter the resulting off-white solid
  5. washwash with hexane (10 mL)
  6. extractionPartition aqueous/ethanolic filtrate between water/EtOAc (4:1) and extract aqueous phase with EtOAc (2×25 mL)
  7. dry with materialDry the combined organic extracts over Na2SO4
  8. concentrationconcentrate in vacuo
  9. filtrationwith filtered solid from crude
  10. customreaction mixture

Sources & evidence

ORD record
ord-63b73521cbe64a8ca6d7cfdd02beca25
Source dataset
uspto-grants-2014_03
Patent number
US08680091B2

Reaction notes

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