3-Bromopropylamine hydrobromide → HCID 85445243, compound

HRID 1732597Notes

Reaction equation

HRID 1732597 reaction equation
[Na].[N+:2]([CH:5]=[C:6](SC)[S:7]([CH3:9])=O)([O-:4])=[O:3].Br.[Br:13][CH2:14][CH2:15][CH2:16][NH2:17]>CO>[N+:2]([CH:5]=[C:6]([S:7][CH3:9])[NH:17][CH2:16][CH2:15][CH2:14][Br:13])([O-:4])=[O:3]

Participants

5

Reactant 3

HCID 787013-Bromopropylamine hydrobromideHCID 5360545SodiumHCID 544870941-Nitro2-methylthio-2-methylsulphinylethylene

Product 1

HCID 85445243HCID 85445243, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of sodium (0.09 g, 0.004 mol) in methanol (10 ml) was added dropwise to a stirred solution of 1-nitro-2-methylthio-2-methylsulphinyl-ethylene (0.5 g, 0.003 mol) and 3-bromopropylamine hydrobromide (0.9 g, 0.004 mol) in methanol (30 ml). The mixture was stirred for 5 hours, and then the solvent was removed in vacuo. The residue was dissolved in water (20 ml) and extracted with chloroform (2×30 ml). The extracts were combined, dried, and concentrated in vacuo. The solid residue was recrystallised from propan-2-ol to give 1-nitro-2-methylthio-2-(3-bromopropylamino)ethylene (0.3 g, 43%) m.p. 92°-92.5°.

Workup

  1. customthe solvent was removed in vacuo
  2. dissolutionThe residue was dissolved in water (20 ml)
  3. extractionextracted with chloroform (2×30 ml)
  4. customdried
  5. concentrationconcentrated in vacuo
  6. customThe solid residue was recrystallised from propan-2-ol

Sources & evidence

ORD record
ord-c624501993cf42b09aa9740bb8579753
Source dataset
uspto-grants-1980_12
Patent number
US04238493

Reaction notes

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