Oxygen → HCID 12467353, compound

HRID 1019325Notes

Reaction equation

HRID 1019325 reaction equation
[CH2:1]([N:3](C)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)C.[C-:11]#[N:12].[Na+].O=O.C(=O)(O)[O-].[Na+].CO.[C:23](O)(=O)[CH3:24]>>[CH3:1][N:3]([CH:23]([CH3:24])[C:11]#[N:12])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 5

HCID 977Oxygen3×HCID 8929Sodium CyanideHCID 11956Benzenamine, N-ethyl-N-methyl-HCID 516892Sodium BicarbonateHCID 10129899Acetic acid methanol

Product 1

HCID 12467353HCID 12467353, compound

Conditions

Temperature
60 °C

Procedure

N-ethyl-N-methylaniline (1 mmol), RuCl3-nH2O (0.05 mmol) and sodium cyanide (1.2 mmol) were charged into a 25-ml side-arm flask, the interior of the reacting container was replaced by oxygen, and an oxygen balloon was attached to supply oxygen at 1 atm. Then, 1.7 ml of a mixed solvent of methanol-acetic acid (volume ratio 3/1) was added thereto at room temperature. Reaction was effected by stirring the mixed liquid at 60° C. for 24 hours. After the reaction mixture liquid was made alkaline with the addition of saturated sodium bicarbonate aqueous solution, the mixture was extracted with 10 ml ethyl acetate once and with 5 ml ethyl acetate twice. The extracted liquid thus obtained was washed with saturated saline solution, and dried over sodium sulfate, thereby obtaining an ethyl acetate solution of N-phenyl-N-ethylaminoacetonitrile and 2-(N-methyl-N-phenylamino)propionitrile. This solution was analyzed by a gas chromatography internal standard method, which revealed the conversion rate of N-ethyl-N-methylaniline being 70% with a yield of N-phenyl-N-ethylaminoacetonitrile being 57% (vs. N-ethyl-N-methylaniline) and that of 2-(N-methyl-N-phenylamino)propionitrile being 7% (vs. N-ethyl-N-methylaniline).

Workup

  1. customat room temperature
  2. customReaction
  3. extractionthe mixture was extracted with 10 ml ethyl acetate once
  4. customThe extracted liquid thus obtained
  5. washwas washed with saturated saline solution
  6. dry with materialdried over sodium sulfate

Sources & evidence

ORD record
ord-0c48018a8b5040f1ac1989a6922b3099
Source dataset
uspto-grants-2002_11
Patent number
US06486340B2

Reaction notes

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