Hydrochloric Acid → HCID 22151847, compound

HRID 703271Notes

Reaction equation

HRID 703271 reaction equation
C[N:2]([CH3:7])[CH:3]=[CH:4][CH:5]=[O:6].Cl.[Cl:9][C:10]1[C:19]([Cl:20])=[CH:18][CH:17]=[CH:16][C:11]=1[C:12](=O)CN.CC[O-].[Na+].Cl>C(O)C>[CH:5]([C:4]1[C:12]([C:11]2[CH:16]=[CH:17][CH:18]=[C:19]([Cl:20])[C:10]=2[Cl:9])=[CH:7][NH:2][CH:3]=1)=[O:6]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 791253-(Dimethylamino)-2-propenalHCID 2723922Sodium ethoxideHCID 22151845Ethanone, 2-amino-1-(2,3-dichlorophenyl)-, hydrochloride

Product 1

HCID 22151847HCID 22151847, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

5.4 g of 3-dimethylaminoacrolein, 3.2 g of 2,3-dichlorophenacylamine hydrochloride and 60 ml of ethanol are heated for 11/2 hours under reflux. Then a solution of sodium ethylate in ethanol (prepared from 1 g of sodium and 15 ml of ethanol) is added dropwise and the reaction mixture is heated under reflux for another 30 minutes. After it has cooled to room temperature, the reaction mixture is poured onto ice/water and neutralised with hydrochloric acid. The precipitate is washed with water, dried in vacuo, and the dry residue is purified by column chromatography (silica gel; elution with a 4:1 mixture of toluene/ethyl acetate). M.p. 152°-154° C. IR (solid/KBr) in cm-1 : 1655 (CO). 1H-NMR (CDCl3) in ppm: 7.0 (broad s, 1H); 7.3 (m, 2H); 9.66 (s, 1H); 11.9 (s, 1H, H replaceable with D2O). Mass peak at 204. This substance is novel, has fungicidal activity, and falls within the ambit of the invention.

Workup

  1. temperatureunder reflux
  2. temperaturethe reaction mixture is heated
  3. temperatureunder reflux for another 30 minutes
  4. washThe precipitate is washed with water
  5. customdried in vacuo
  6. customthe dry residue is purified by column chromatography (silica gel
  7. washelution
  8. additionwith a 4:1 mixture of toluene/ethyl acetate)

Sources & evidence

ORD record
ord-bdbf6c1e9831473fa63faddf79e0221b
Source dataset
uspto-grants-1991_01
Patent number
US04981990

Reaction notes

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