Phenethyl bromide → HCID 17135006, compound

HRID 850050Notes

Reaction equation

HRID 850050 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([NH2:7])=[O:6].C(=O)([O-])[O-].[K+].[K+].Br[CH2:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C(#N)C.O>[CH2:18]([O:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([NH2:7])=[O:6])[CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 3

HCID 7666Phenethyl bromideHCID 11430Potassium CarbonateHCID 3424033-Hydroxybenzamide

Product 1

HCID 17135006HCID 17135006, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

3-Hydroxybenzamide (500 mg; 3.6 mM) was dissolved in dry acetonitrile (36 ml), and to this was added potassium carbonate (0.503 g; 3.6mmol) and 2-(bromoethyl)benzene (0.498 ml; 3.6 mmol). The mixture was heated under reflux for two days. The acetonitrile was removed under reduced pressure to yield a white solid. This was dissolved in water and extracted into dichloromethane (3×30 ml). The organics were pooled, dried over magnesium sulphate, filtered and the solvent was removed under reduced pressure to yield a white solid. This was recrystallised from boiling ethyl acetate and petrol (0.459 g; 12.51%). MPt: 132-136° C. 1H: 200 MHz CDCl3 3.05 (2H, t, H8); 4.2 (2H, t, H7); 6.00 (1H, br s, NH); 7.04 (1H, m, H4); 7.27 (9H, m, NH; aromatic). IR cm-1 3300 (NH2); 1666 (CO); 2930 (C=C). M/Z (EI); 241 (M+ ; 18%); 105 (--COHN2 ; 100%). Elemental Analysis: Expected % C15H15O2N C: 74.4, H: 6.20, N: 5.79; Found: % C: 74.7, H:6.2, N:5.8.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for two days
  3. customThe acetonitrile was removed under reduced pressure
  4. customto yield a white solid
  5. extractionextracted into dichloromethane (3×30 ml)
  6. dry with materialdried over magnesium sulphate
  7. filtrationfiltered
  8. customthe solvent was removed under reduced pressure
  9. customto yield a white solid
  10. customThis was recrystallised
  11. custom132-136° C

Sources & evidence

ORD record
ord-c5574f0417f2485c8c87f12754c59c33
Source dataset
uspto-grants-2000_01
Patent number
US06015827

Reaction notes

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