Ethanimidic acid, ethyl ester, hydrochloride (1:1) → HCID 178432593, compound

HRID 1155551Notes

Reaction equation

HRID 1155551 reaction equation
[CH3:1][N:2]([CH3:18])[C:3]1[CH:8]=[C:7]([C:9](OCC)(OCC)[CH2:10][NH2:11])[CH:6]=[CH:5][N:4]=1.Cl.[C:20](=[NH:25])(OCC)[CH3:21]>C(O)C>[CH3:18][N:2]([CH3:1])[C:3]1[CH:8]=[C:7]([C:9]2[N:25]=[C:20]([CH3:21])[NH:11][CH:10]=2)[CH:6]=[CH:5][N:4]=1

Participants

4

Reactant 2

HCID 2724290Ethanimidic acid, ethyl ester, hydrochloride (1:1)HCID 20561085HCID 20561085, compound

Product 1

HCID 178432593HCID 178432593, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1.0 g. (4 mmoles) of 2-(2-dimethylamino-4-pyridyl)-2,2-diethoxyethylamine, 500 mg. (4.1 mmoles) of ethyl acetimidate hydrochloride and 15 ml. of ethanol is heated to reflux for 1.5 hours. The mixture is concentrated, and the residue taken up in 10 ml. of concentrated hydrochloric acid. After heating at steam bath temperatures for 1 hour, the cooled acid solution is made basic by the addition of solid sodium carbonate, and the product is extracted with chloroform (3×10 ml.). The combined extracts are dried and concentrated to give the crude product, which is purified further by chromatographing on silica-gel using chloroform-methanol as the eluent.

Workup

  1. additionA mixture of 1.0 g
  2. temperatureto reflux for 1.5 hours
  3. concentrationThe mixture is concentrated
  4. temperatureAfter heating at steam bath temperatures for 1 hour
  5. additionthe cooled acid solution is made basic by the addition of solid sodium carbonate
  6. extractionthe product is extracted with chloroform (3×10 ml.)
  7. customThe combined extracts are dried
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-d110f2bc9c174278aebb4a9e4e5ac532
Source dataset
uspto-grants-1981_11
Patent number
US04302464

Reaction notes

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