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

HRID 2041166Notes

Reaction equation

HRID 2041166 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].[C:13]([NH2:16])(=[S:15])[CH3:14].C(=O)(O)[O-].[Na+]>C(O)C.CCOCC.CCCCCC>[CH3:14][C:13]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:16]=1

Participants

6

Reactant 3

HCID 986544-(Bromoacetyl)benzonitrileHCID 516892Sodium BicarbonateHCID 2723949Thioacetamide

Product 1

HCID 7163534-(2-methyl-1,3-thiazol-4-yl)benzonitrileYield 93%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 21584099Diethylether hexaneSolvent

Procedure

Suspend 4-cyanophenacyl bromide (515 mg, 2.23 mmol) in ethanol (15 mL). Add thioacetamide (171 mg, 2.23 mmol) and sodium bicarbonate (187 mg, 2.23 mmol) and heat the mixture under reflux for 2 h. Concentrate in vacuo and dissolve the residue in DCM. Wash the organic fraction with water, dry over Na2SO4, filter and concentrate to give a solid. Suspend the solid in ether/hexane and filter under vacuum washing with hexane to obtain the desired intermediate as a white solid (415 mg, 93%). GC-MS m/z: 200 (M+).

Workup

  1. temperatureunder reflux for 2 h
  2. concentrationConcentrate in vacuo
  3. dissolutiondissolve the residue in DCM
  4. washWash the organic fraction with water
  5. dry with materialdry over Na2SO4
  6. filtrationfilter
  7. concentrationconcentrate
  8. customto give a solid
  9. filtrationfilter under vacuum
  10. washwashing with hexane

Sources & evidence

ORD record
ord-5dcf51b07eeb478bae9d88d8dba2271a
Source dataset
uspto-grants-2013_11
Patent number
US08580780B2

Reaction notes

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