Calcium Carbonate → 3-(N-2-hydroxyethyl-N-methylamino)benzonitrile

HRID 591140Notes

Reaction equation

HRID 591140 reaction equation
[CH3:1][NH:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[C:6]#[N:7].Br[CH2:12][CH2:13][OH:14].C([O-])([O-])=O.[Ca+2]>O>[OH:14][CH2:13][CH2:12][N:2]([CH3:1])[C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[C:6]#[N:7]

Participants

5

Reactant 3

HCID 10112Calcium CarbonateHCID 108982-BromoethanolHCID 177940363-(Methylamino)benzonitrile

Product 1

HCID 586560573-(N-2-hydroxyethyl-N-methylamino)benzonitrileYield 76.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3-methylaminobenzonitrile (11.36 g, 86 mmol, 1.0 eq), 2-bromoethanol (43.00 g, 344 mmol, 4.0 eq) and CaCO3 (34.40 g, 344 mmol, 4.0 eq) are added into water (150 ml) at room temperature, and the resulting mixture is refluxed with elevated temperature for 13.5 h, then cooled and filtered, and the aqueous solution is extracted with ethyl acetate (100 ml*3). The organic phases are combined, washed with water (20 ml*2), washed with saturated brine twice, dried over anhydrous sodium sulfate, and concentrated to give a light yellow oily crude product (11.55 g, crude yield: 76.2%). The crude product can be used directly in next step without purification.

Workup

  1. temperaturethe resulting mixture is refluxed with elevated temperature for 13.5 h
  2. temperaturecooled
  3. filtrationfiltered
  4. extractionthe aqueous solution is extracted with ethyl acetate (100 ml*3)
  5. washwashed with water (20 ml*2)
  6. washwashed with saturated brine twice
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-31b0e4c7b5044d5c854abf29dd9e66ae
Source dataset
uspto-grants-2016_01
Patent number
US09238632B2

Reaction notes

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