Sodium Cyanide → HCID 86735627, compound

HRID 2083395Notes

Reaction equation

HRID 2083395 reaction equation
C(O)(=O)/C=C\C(O)=O.[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:19].[C-:30]#[N:31].[Na+]>O.[OH-].[Na+].CCOCC>[ClH:19].[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][C:30]#[N:31]

Participants

6

Reactant 2

HCID 8929Sodium CyanideHCID 86735629HCID 86735629, compound

Product 1

HCID 86735627HCID 86735627, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 14798Sodium HydroxideSolvent2×

Procedure

10 Mmol (4.3 g) of 5-chloro-4'-trifluoromethylvalerophenone O-(2-aminoethyl) oxime maleate (1:1) (melting point 121.5°-122.5° C) were dissolved in 50 ml of water. 5 Ml of 50% sodium hydroxide solution at 0° C were added. Three extractions with 25 ml of CH2Cl2 were then carried out and this extract was washed with 5% sodium bicarbonate solution (1x) and water (1x). The solution was then dried on sodium sulphate and the CH2Cl2 was distilled off in vacuo. The residue was dissolved in 10 ml of dimethylsulfoxide (DMSO) and 25 mmol (1.2 g) of sodium cyanide were then added. The suspension was heated at a temperature of 50° to 70° C for 3 hours and then cooled to room temperature. Then there was diluted with 100 ml of 0.5 N sodium hydroxide solution and three extractions with 40 ml of ether were carried out. The ether extract was washed with water (1x), dried on sodium sulphate and evaporated in vacuo. The residue was purified chromatographically over silica gel with ethanol/ammonia (95:5) as an eluent. After evaporating the solvents, the residue was dissolved in absolute ethanol and acidified with ethanolic hydrochloric acid. After crystallization from ethanol/ether (1:3) the title compound having a melting point of 142°-143.5° C was obtained.

Workup

  1. extractionThree extractions with 25 ml of CH2Cl2
  2. washthis extract was washed with 5% sodium bicarbonate solution (1x) and water (1x)
  3. customThe solution was then dried on sodium sulphate
  4. distillationthe CH2Cl2 was distilled off in vacuo
  5. dissolutionThe residue was dissolved in 10 ml of dimethylsulfoxide (DMSO)
  6. temperatureThe suspension was heated at a temperature of 50° to 70° C for 3 hours
  7. extractionThe ether extract
  8. washwas washed with water (1x)
  9. customdried on sodium sulphate
  10. customevaporated in vacuo
  11. customThe residue was purified chromatographically over silica gel with ethanol/ammonia (95:5) as an eluent
  12. customAfter evaporating the solvents
  13. dissolutionthe residue was dissolved in absolute ethanol
  14. customAfter crystallization from ethanol/ether (1:3) the title compound
  15. customwas obtained

Sources & evidence

ORD record
ord-38cc84c99b1747ff86778b3e9c5f7040
Source dataset
uspto-grants-1978_04
Patent number
US04085225

Reaction notes

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