Hydrochloric Acid → Methyl 3-methoxypropanimidate--hydrogen chloride (1/1)

HRID 2420032Notes

Reaction equation

HRID 2420032 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][C:5]#[N:6].[CH3:7][OH:8].[ClH:9]>C1(C)C=CC=CC=1>[ClH:9].[CH3:7][O:8][C:5](=[NH:6])[CH2:4][CH2:3][O:2][CH3:1]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 610323-Methoxypropionitrile

Product 1

HCID 10149010Methyl 3-methoxypropanimidate--hydrogen chloride (1/1)Yield 80%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
3 °C

Procedure

To a 3-necked reaction vessel equipped with stirrer, gas delivery tube, thermometer and reflux condenser is charged 85.1 parts of 3-methoxypropionitrile, 32.0 parts of reagent grade methanol and 300 parts of toluene. The exit from the reflux condenser is connected to a drying tower filled with a commercially available drying agent and a bath is provided for cooling the vessel below 0° C. Hydrochloric acid gas flow is controlled by means of a rotameter and is passed through a calcium chloride filled trap which serves both as a means for drying the gas and as a receiver in case liquid is sucked back into the line. After charging the reagents and toluene, the solution is stirred and cooled to 3° C. and the HCl gas is then fed, while controlling the temperature to -4° to 1° C., until 38.0 parts have been added. The HCl gas is added as rapidly as possible commensurate with complete adsorption and good temperature control. The mixture is then stirred for 15 hours in an ice bath (maximum 10° C.). Crystals of methyl-3-methoxypropionimidate hydrochloride appear 2.25 hours after the HCl addition is complete. 46.5 Hours after the HCl addition is stopped, an 80% yield of methyl-3-methoxypropionimidate hydrochloride is formed.

Workup

  1. customTo a 3-necked reaction vessel equipped with stirrer, gas delivery tube
  2. temperaturethermometer and reflux condenser
  3. additionfilled with a commercially available drying agent
  4. customa bath is provided
  5. temperaturefor cooling the vessel below 0° C
  6. customis passed through a calcium chloride filled trap
  7. customfor drying the gas
  8. customto -4° to 1° C.
  9. additionuntil 38.0 parts have been added
  10. additionThe HCl gas is added as rapidly as possible commensurate with complete adsorption and good temperature control
  11. stirringThe mixture is then stirred for 15 hours in an ice bath (maximum 10° C.)
  12. additionafter the HCl addition
  13. addition46.5 Hours after the HCl addition

Sources & evidence

ORD record
ord-275054c75f3f484cb8f943d6960f0c48
Source dataset
uspto-grants-1978_08
Patent number
US04108883

Reaction notes

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