Hydrochloric Acid → HCID 86735631, compound

HRID 2083396Notes

Reaction equation

HRID 2083396 reaction equation
[C:1]([OH:8])(=[O:7])/[CH:2]=[CH:3]\[C:4]([OH:6])=[O:5].[NH2:9][CH2:10][CH2:11][O:12][N:13]=[C:14]([C:20]1[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][CH:21]=1)[CH2:15][CH2:16][CH2:17][CH2:18]Cl.[Na].Cl>C(O)C>[C:1]([OH:8])(=[O:7])/[CH:2]=[CH:3]/[C:4]([OH:6])=[O:5].[NH2:9][CH2:10][CH2:11][O:12][N:13]=[C:14]([C:20]1[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][CH:21]=1)[CH2:15][CH2:16][CH2:17][CH2:18][O:5][CH2:4][CH3:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 5360545SodiumHCID 86735629HCID 86735629, compound

Product 1

HCID 86735631HCID 86735631, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

12 Mmol (5.1 g) of 5-chloro-4'-trifluoromethylvalerophenone O-(2-aminoethyl) oxime maleate (1:1) (melting point 121.5°-122.5° C) were added to a solution of 240 mgat. (5.5 g) of sodium in 100 ml of absolute ethanol. The mixture was heated at 70° C for 8 hours followed by neutralization at 0° C with alcoholic hydrochloric acid and the sodium chloride was filtered off. The alcohol was distilled off in vacuo and the residue was dissolved in water. 5 Ml of 50% sodium hydroxide solution were added to this solution and three extractions with 40 ml of ether were then carried out. The ether extract was washed with 5% sodium bicarbonate solution (1x) and with water (1x), followed by drying on sodium sulphate. The ether was distilled off in vacuo and the residue was dissolved in absolute ethanol. The solution was acidified with an equimolar quantity of fumaric acid. The title compound crystallized from the solution. Melting point 105°-105.5° C.

Workup

  1. filtrationthe sodium chloride was filtered off
  2. distillationThe alcohol was distilled off in vacuo
  3. dissolutionthe residue was dissolved in water
  4. addition5 Ml of 50% sodium hydroxide solution were added to this solution and three extractions with 40 ml of ether
  5. extractionThe ether extract
  6. washwas washed with 5% sodium bicarbonate solution (1x) and with water (1x)
  7. customby drying on sodium sulphate
  8. distillationThe ether was distilled off in vacuo
  9. dissolutionthe residue was dissolved in absolute ethanol
  10. customThe title compound crystallized from the solution

Sources & evidence

ORD record
ord-362b7be32ad447fb8d51e213d8cd7c52
Source dataset
uspto-grants-1978_04
Patent number
US04085225

Reaction notes

Loading…