Phenacyl bromide → HCID 178424201, compound

HRID 1462190Notes

Reaction equation

HRID 1462190 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([NH2:6])=[NH:5].Br[CH2:12][C:13]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=O>C(Cl)(Cl)Cl>[C:15]1([C:13]2[N:5]=[C:4]([C:3]3[CH:7]=[CH:8][CH:9]=[CH:10][C:2]=3[CH3:1])[NH:6][CH:12]=2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 6259Phenacyl bromideHCID 5764802-Methyl-benzamidine

Product 1

HCID 178424201HCID 178424201, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a solution of 6.1 g (0.0455 mole) of 2-methylbenzamidine in 25 ml of chloroform 3.6 g (0.018 mole) of α-bromoacetophenone were added and the resulting mixture was refluxed for four hours. After cooling and adding 50 ml of chloroform the reaction mixture was first washed with diluted ammonia and then with water and subsequently dried over sodium sulfate. The sodium sulfate was removed by filtration and the filtrate was chromatographed through silica gel by eluting with mixtures of CHCl3 /CH3COOC2H5 containing up to a maximum of 4% (in volume) of CH3COOC2H5. The fractions eluted with CH3Cl3 /CH3COOC2H5 =9/1 (v/v) were collected, the solvent was evaporated off and the residue was crystallized from diethylether/light petroleum. Yield 1.95 g (46.3%) of the title compound M.p. 145°-46° C.

Workup

  1. temperaturethe resulting mixture was refluxed for four hours
  2. temperatureAfter cooling
  3. washwas first washed with diluted ammonia
  4. dry with materialwith water and subsequently dried over sodium sulfate
  5. customThe sodium sulfate was removed by filtration
  6. customthe filtrate was chromatographed through silica gel
  7. washby eluting with mixtures of CHCl3 /CH3COOC2H5 containing up to a maximum of 4% (in volume) of CH3COOC2H5
  8. washThe fractions eluted with CH3Cl3 /CH3COOC2H5 =9/1 (v/v)
  9. customwere collected
  10. customthe solvent was evaporated off
  11. customthe residue was crystallized from diethylether/light petroleum

Sources & evidence

ORD record
ord-eff9eb35624647c7931d01ea03843631
Source dataset
uspto-grants-1984_07
Patent number
US04459302

Reaction notes

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