Ethylenediamine → HCID 90411645, compound

HRID 1521932Notes

Reaction equation

HRID 1521932 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[C:5]#[N:6].[S].[CH2:13](N)[CH2:14][NH2:15]>>[Br:1][C:2]1[CH:3]=[C:4]([C:5]2[NH:15][CH2:14][CH2:13][N:6]=2)[CH:7]=[CH:8][C:9]=1[O:10][CH3:11]

Participants

4

Reactant 3

HCID 3301EthylenediamineHCID 7360493-Bromo-4-methoxybenzonitrileHCID 5362487Sulfur

Product 1

HCID 90411645HCID 90411645, compound

Conditions

Temperature
110 °C

Procedure

To a solution of 3-bromo-4-methoxybenzonitrile (1 g, 4.72 mmol) in 10 mL of ethane-1,2-diamine was added sulfur (0.121 g, 3.77 mmol) and the mixture was heated at 110° C. overnight. The mixture was cooled, quenched with water and extracted with ethyl acetate. The organic layer was washed with water and brine (25 mL each), dried over sodium sulfate, filtered, and concentrated to afford the title compound. LCMS: 257 (M+2)+.

Workup

  1. temperatureThe mixture was cooled
  2. customquenched with water
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with water and brine (25 mL each)
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-ba598037833c4653b6a96a54587b4156
Source dataset
uspto-grants-2015_07
Patent number
US09073922B2

Reaction notes

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