4-(Bromoacetyl)benzonitrile → HCID 59828836, compound

HRID 1191076Notes

Reaction equation

HRID 1191076 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].[F:13][C:14]([F:21])([F:20])[CH2:15][NH:16][C:17]([NH2:19])=[S:18].C(=O)(O)[O-].[Na+]>C(O)C>[F:13][C:14]([F:21])([F:20])[CH2:15][NH:16][C:17]1[S:18][CH:8]=[C:7]([C:6]2[CH:11]=[CH:12][C:3]([C:1]#[N:2])=[CH:4][CH:5]=2)[N:19]=1

Participants

5

Reactant 3

HCID 986544-(Bromoacetyl)benzonitrileHCID 516892Sodium BicarbonateHCID 202028121-(2,2,2-Trifluoroethyl)thiourea

Product 1

HCID 59828836HCID 59828836, compoundYield 95.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Slurry 4-cyanophenacyl bromide (1.4 g, 6.3 mmol), 2,2,2-trifluoroethyl-thiourea (1.0 g, 6.3 mmol) and sodium bicarbonate (529 mg, 6.3 mmol) in absolute ethanol (30 mL). Stir the mixture at reflux for 1 h under a nitrogen atmosphere. Cool to room temperature and concentrate in vacuo. Partition the residue between DCM (100 mL) and water (20 mL). Dry the organic layer over Na2SO4 and concentrate in vacuo to obtain the desired intermediate (1.7 g, 95%). MS (ES+) m/z: 284 (M+H)+.

Workup

  1. temperatureat reflux for 1 h under a nitrogen atmosphere
  2. concentrationconcentrate in vacuo
  3. customPartition the residue between DCM (100 mL) and water (20 mL)
  4. dry with materialDry the organic layer over Na2SO4
  5. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-d4a371b13503439f922b45fee5d47658
Source dataset
uspto-grants-2014_03
Patent number
US08680091B2

Reaction notes

Loading…