Hydrochloric Acid → n-(4-Cyanophenyl)-n-methylglycine

HRID 2394223Notes

Reaction equation

HRID 2394223 reaction equation
F[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.[CH3:10][NH:11][CH2:12][C:13]([OH:15])=[O:14].C(=O)([O-])[O-].[K+].[K+].Cl>CS(C)=O.O>[C:6]([C:5]1[CH:8]=[CH:9][C:2]([N:11]([CH3:10])[CH2:12][C:13]([OH:15])=[O:14])=[CH:3][CH:4]=1)#[N:7]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 1088SarcosineHCID 11430Potassium CarbonateHCID 145174-Fluorobenzonitrile

Product 1

HCID 18412499n-(4-Cyanophenyl)-n-methylglycine

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent2×

Conditions

Temperature
100 °C

Procedure

In a 500-ml pear-shaped flask, 4-fluorobenzonitrile (10.44 g, 86.26 mmoles), N-methylglycine (8.45 g, 94.89 mmoles) and potassium carbonate (14.28 g, 103.48 mmoles) were placed, followed by addition of 200 ml of dimethylsulfoxide as a solvent. A water cooling pipe was attached to the flask, and the reaction was carried out with heating on an oil bath heated at 100° C. for 9 hours with stirring using a magnetic stirrer. After cooling naturally, the reaction mixture was dissolved in 1 liter of water and subjected to acidolysis with 1/10N HCl, followed by filtration of a precipitate. After washing with water well, the precipitate was washed with hexane/benzene (4/1 in volume ratio). The yield of the product after dried was 14.21 g (74.79 mmoles, 86.7%). The melting point was 64.5° C.

Workup

  1. temperaturewith heating on an oil bath
  2. temperatureAfter cooling naturally
  3. filtrationfollowed by filtration of a precipitate
  4. washAfter washing with water well
  5. washthe precipitate was washed with hexane/benzene (4/1 in volume ratio)
  6. customThe yield of the product after dried

Sources & evidence

ORD record
ord-f4dab072ba34466a863ee15519aa1673
Source dataset
uspto-grants-1998_09
Patent number
US05811218

Reaction notes

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