Aminoacetaldehyde dimethyl acetal → HCID 178495904, compound

HRID 1668963Notes

Reaction equation

HRID 1668963 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=O)[S:5][C:6]=1[CH3:7].[CH3:10][O:11][CH:12]([O:15][CH3:16])[CH2:13][NH2:14]>O>[Br:1][C:2]1[CH:3]=[C:4](/[CH:8]=[N:14]/[CH2:13][CH:12]([O:15][CH3:16])[O:11][CH3:10])[S:5][C:6]=1[CH3:7]

Participants

4

Reactant 2

HCID 89728Aminoacetaldehyde dimethyl acetalHCID 155382124-Bromo-5-methylthiophene-2-carbaldehyde

Product 1

HCID 178495904HCID 178495904, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

4-bromo-5-methylthiophene-2-carbaldehyde (11.00 g, 53.6 mmol) was treated with 2,2-dimethoxyethanamine (17.5 ml, 161 mmol) and the mixture stirred at 120° C. for 12 hours. The reaction was poured into water (50 ml) and stirred for 1 hour and extracted with ethyl acetate. The organic layer was washed (2×) with an aqueous saturated solution of sodium bicarbonate, then with water and then brine. The organic layer was then dried with sodium sulfate, concentrated under reduced pressure and placed under a vacuum line to give (E)-N-((4-bromo-5-methylthiophen-2-yl)methylene)-2,2-dimethoxyethanamine.

Workup

  1. stirringstirred for 1 hour
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed (2×) with an aqueous saturated solution of sodium bicarbonate
  4. dry with materialThe organic layer was then dried with sodium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-fad7e031f4174616a9341336251c7f3b
Source dataset
uspto-grants-2011_08
Patent number
US07989461B2

Reaction notes

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