2-Bromoethylamine hydrobromide → HCID 85445244, compound

HRID 1248631Notes

Reaction equation

HRID 1248631 reaction equation
C[O-].[Na+].[Na].[N+:5]([CH:8]=[C:9](SC)[S:10]([CH3:12])=O)([O-:7])=[O:6].Br.[Br:16][CH2:17][CH2:18][NH2:19]>CO>[N+:5]([CH:8]=[C:9]([S:10][CH3:12])[NH:19][CH2:18][CH2:17][Br:16])([O-:7])=[O:6]

Participants

6

Reactant 4

HCID 27742172-Bromoethylamine hydrobromideHCID 5360545SodiumHCID 10942334Sodium MethoxideHCID 544870941-Nitro2-methylthio-2-methylsulphinylethylene

Product 1

HCID 85445244HCID 85445244, compoundYield 6,975.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

(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-nitro2-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 (185 g, 71%) m.p. 123°-126°.

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-bd53ffe8e90e40b3b2190fe4296d9fcd
Source dataset
uspto-grants-1985_06
Patent number
US04525477

Reaction notes

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