Hydrochloric Acid → Methyl 2-phenylethanimidate--hydrogen chloride (1/1)

HRID 1252548Notes

Reaction equation

HRID 1252548 reaction equation
[CH2:1]([C:8]#[N:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:10][OH:11].[ClH:12]>C1(C)C=CC=CC=1>[ClH:12].[C:2]1([CH2:1][C:8](=[NH:9])[O:11][CH3:10])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 8794Phenylacetonitrile

Product 1

HCID 12433430Methyl 2-phenylethanimidate--hydrogen chloride (1/1)Yield 88.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The same equipment as described in Example 3 was used. Benzyl cyanide (38.0 grams; 0.325 mole) was mixed with absolute methanol (10.3 grams; 0.322 mole) and toluene (195 ml). With cooling and agitation HCl gas (16 grams; 0.44 mole) was introduced from a weighed cylinder and the mixture was maintained under the same conditions overnight (26 hours). The resulting white slurry was filtered cold and the solid methyl phenylacetimidate hydrochloride (52.8 grams; 88.4% yield) was collected and a portion of it used directly in the next step.

Workup

  1. temperatureWith cooling
  2. temperaturethe mixture was maintained under the same conditions overnight (26 hours)
  3. filtrationThe resulting white slurry was filtered cold

Sources & evidence

ORD record
ord-562aa400d1424e78a5dc2807f7904397
Source dataset
uspto-grants-1988_05
Patent number
US04743701

Reaction notes

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