2-Bromoethylamine hydrobromide → HCID 13732574, compound

HRID 1731547Notes

Reaction equation

HRID 1731547 reaction equation
[C:1]([S:4][C:5](=[CH:14][N:15]([CH3:17])C)[C:6]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:7])(=O)C.C[O-].[Na+].Br.BrCCN>C(O)C>[C:8]1([C:6]([C:5]2[S:4][CH2:1][CH2:17][NH:15][CH:14]=2)=[O:7])[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 27742172-Bromoethylamine hydrobromideHCID 10942334Sodium Methoxide2×HCID 54527036HCID 54527036, compound

Product 1

HCID 13732574HCID 13732574, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent4×

Procedure

To a solution of 39.56 g (0.16M)α-acetylthio-β-dimethylaminoacrylophenone in 300 ml absolute ethanol stirring under nitrogen at 0° a solution of 8.64 g (0.16M) sodium methoxide in 230 ml ethanol is added dropwise over a period of 15 minutes. After complete addition, the dark red solution is stirred at 0 to -3° for 0.5 hours. To the solution stirring at -3° a solution of 32.79 g (0.16M) 2-bromoethylamine hydrobromide in 270 ml absolute ethanol is added dropwise over a period of 25 minutes. After complete addition the dark solution is stirred at 0° for 0.5 hours, and a solution of 8.64 g (0.16M) sodium methoxide in 230 ml absolute ethanol is added dropwise over a period of 15 minutes. The dark solution is stirred at 0° for 1 hour. The reaction mixture is allowed to warm slowly to 20° . A suspension is formed within an hour of removing the cooling bath. The reaction mixture is stirred for 16 hours at ca 20° . The suspension is cooled to 5° and acidified to pH 2 with 30 ml of a 1:1 mixture of ethanol and concentrated hydrochloric acid. The suspension is concentrated in vacuo to remove all but ca. 100 ml of ethanol. The residue is suspended in 200 ml CHCl3 and the mixture is washed with water and a saturated NaCl solution. The organic layer is concentrated in vacuo to give a partially crystalline residue. This residue is triturated with a 1:1 mixture of ether and ethanol. Orange crystals are collected to give the title compound. M.P. 184°-186.5°.

Workup

  1. additionAfter complete addition
  2. additionis added dropwise over a period of 25 minutes
  3. additionAfter complete addition the dark solution
  4. stirringis stirred at 0° for 0.5 hours
  5. stirringThe dark solution is stirred at 0° for 1 hour
  6. temperatureto warm slowly to 20°
  7. customA suspension is formed within an hour
  8. customof removing the cooling bath
  9. stirringThe reaction mixture is stirred for 16 hours at ca 20°
  10. temperatureThe suspension is cooled to 5°
  11. additionacidified to pH 2 with 30 ml of a 1:1 mixture of ethanol and concentrated hydrochloric acid
  12. concentrationThe suspension is concentrated in vacuo
  13. customto remove all but ca. 100 ml of ethanol
  14. washthe mixture is washed with water
  15. concentrationThe organic layer is concentrated in vacuo
  16. customto give a partially crystalline residue
  17. customThis residue is triturated with a 1:1 mixture of ether and ethanol
  18. customOrange crystals are collected

Sources & evidence

ORD record
ord-9405df76511840e1b4d744a8cb0346a9
Source dataset
uspto-grants-1986_11
Patent number
US04622322

Reaction notes

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