2-Bromoethylamine hydrobromide → HCID 85445244, compound

HRID 1995587Notes

Reaction equation

HRID 1995587 reaction equation
C[O-].[Na+].[N+:4]([CH:7]=[C:8](SC)[S:9]([CH3:11])=O)([O-:6])=[O:5].Br.[Br:15][CH2:16][CH2:17][NH2:18]>CO>[N+:4]([CH:7]=[C:8]([S:9][CH3:11])[NH:18][CH2:17][CH2:16][Br:15])([O-:6])=[O:5]

Participants

5

Reactant 3

HCID 27742172-Bromoethylamine hydrobromideHCID 10942334Sodium MethoxideHCID 544870941-Nitro2-methylthio-2-methylsulphinylethylene

Product 1

HCID 85445244HCID 85445244, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(b)(i) A solution of sodium methoxide (sodium (0.3 g, 0.013 mol) in methanol (10 ml)) was added dropwise, over a period of 10 minutes to a stirred mixture of 1-nitro-2-methylthio-2-methylsulphinylethylene (2 g, 0.011 mol) and 2-bromoethylamine hydrobromide (2.7 g, 0.013 mol) in methanol (25 ml), cooled to 0°. The solution was stirred at 0° for a further 15 minutes, and then it was allowed to attain room temperature. After 1 hour, the solvent was removed in vacuo, and the semi-solid residue was extracted with hot chloroform (2×25 ml). The extracts were combined and concentrated in vacuo. The solid residue was recrystallised from propan-2-ol to give 1-nitro-2-methylthio-2-(2-bromoethylamino)ethylene (1.85 g, 71%) m.p. 123°-126°. Found: C, 25.1; H, 3.7; N, 11.8; S, 13.6; Br, 33.3; C5H9BrN2O2S requires: C, 24.9; H, 3.8; N, 11.6; S, 13.3; Br, 33.1%.

Workup

  1. temperaturecooled to 0°
  2. customto attain room temperature
  3. waitAfter 1 hour
  4. customthe solvent was removed in vacuo
  5. extractionthe semi-solid residue was extracted with hot chloroform (2×25 ml)
  6. concentrationconcentrated in vacuo
  7. customThe solid residue was recrystallised from propan-2-ol

Sources & evidence

ORD record
ord-8ef17b31cd704b668e495b41496f4587
Source dataset
uspto-grants-1983_09
Patent number
US04405624

Reaction notes

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