Sodium borohydride → N-((4-bromo-5-methylthiophen-2-yl)methyl)-2,2-dimethoxyethanamine

HRID 1668964Notes

Reaction equation

HRID 1668964 reaction equation
[Br:1][C:2]1[CH:3]=[C:4](/[CH:8]=[N:9]/[CH2:10][CH:11]([O:14][CH3:15])[O:12][CH3:13])[S:5][C:6]=1[CH3:7].[BH4-].[Na+]>CCO>[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][NH:9][CH2:10][CH:11]([O:14][CH3:15])[O:12][CH3:13])[S:5][C:6]=1[CH3:7]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 178495904HCID 178495904, compound

Product 1

HCID 58466475N-((4-bromo-5-methylthiophen-2-yl)methyl)-2,2-dimethoxyethanamine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(E)-N-((4-bromo-5-methylthiophen-2-yl)methylene)-2,2-dimethoxyethanamine (15.00 g, 51.34 mmol) was taken up in EtOH (50 ml) and treated with sodium borohydride (1.942 g, 51.34 mmol) slowly (some fizzing observed). The reaction was stirred at reflux for 3 hours and at room temperature overnight. The reaction was then concentrated under reduced pressure and the residue was taken up in a mixture of ethyl acetate and water. The layer were separated and the organic layer washed (2×) with an aqueous saturated solution of sodium bicarbonate, then with water and then brine. The organic layer was dried with sodium sulfate and concentrated under reduced pressure to give N-((4-bromo-5-methylthiophen-2-yl)methyl)-2,2-dimethoxyethanamine as a brown oil. MS (M+1) 295.

Workup

  1. concentrationThe reaction was then concentrated under reduced pressure
  2. additionthe residue was taken up in a mixture of ethyl acetate and water
  3. customThe layer were separated
  4. washthe organic layer washed (2×) with an aqueous saturated solution of sodium bicarbonate
  5. dry with materialThe organic layer was dried with sodium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-db5f9c9317454c968544f40082fcd41c
Source dataset
uspto-grants-2011_08
Patent number
US07989461B2

Reaction notes

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