Water → HCID 18972725, compound

HRID 2394317Notes

Reaction equation

HRID 2394317 reaction equation
[H-].[Na+].[NH2:3][C:4]([CH3:8])([CH3:7])[CH2:5][OH:6].Cl[C:10]1[CH:17]=[CH:16][C:13]([C:14]#[N:15])=[CH:12][CH:11]=1.O>CN(C)C=O>[C:14]([C:13]1[CH:16]=[CH:17][C:10]([O:6][CH2:5][C:4]([NH2:3])([CH3:8])[CH3:7])=[CH:11][CH:12]=1)#[N:15]

Participants

6

Reactant 4

HCID 962WaterHCID 118072-Amino-2-methyl-1-propanolHCID 121634-ChlorobenzonitrileHCID 24758Sodium hydride

Product 1

HCID 18972725HCID 18972725, compoundYield 79.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4.0 g of 60% sodium hydride was added to a solution containing 8.9 g of 2-amino-2-methyl-1-propanol dissolved in 100 ml of N,N-dimethylformamide in an ice bath. After the reaction mixture was stirred for 30 minutes at room temperature, 13.7 g of 4-chlorobenzonitrile was added to the reaction mixture and the reaction mixture was stirred for 15 hours at room temperature. The reaction mixture was poured into water. The organic layer of the reaction mixture was extracted with ethyl acetate, washed with water, and then dried over anhydrous magnesium sulfate. After the solvent was removed under reduced pressure. The fraction possessing a low boiling point was removed from the residue, thus obtaining 15 g of the desired product (yield: 79%).

Workup

  1. stirringthe reaction mixture was stirred for 15 hours at room temperature
  2. extractionThe organic layer of the reaction mixture was extracted with ethyl acetate
  3. washwashed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customAfter the solvent was removed under reduced pressure
  6. customwas removed from the residue

Sources & evidence

ORD record
ord-604af3a326b54aa6b77dcae982c0d17f
Source dataset
uspto-grants-1998_09
Patent number
US05811424

Reaction notes

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