Ammonia → HCID 19424083, compound

HRID 35933Notes

Reaction equation

[Cl-].[NH4+:2].[C-:3]#[N:4].[Na+].N.[CH3:7][C:8]([C:11]1[CH:20]=[CH:19][C:14]([O:15][CH2:16][CH:17]=O)=[CH:13][CH:12]=1)([CH3:10])[CH3:9]>CO.O>[NH2:2][CH:17]([CH2:16][O:15][C:14]1[CH:19]=[CH:20][C:11]([C:8]([CH3:10])([CH3:9])[CH3:7])=[CH:12][CH:13]=1)[C:3]#[N:4]

Participants

Conditions

Temperature: 10 °C

Procedure

To a mixture of 2.92 g (54.6 mmol.) of ammonium chloride, 2.47 g (50.4 mmol.) of sodium cyanide and 18 ml (296 mmol.) of a 28% aqueous solution of ammonia, there was added dropwise a solution of the wet cake of 2-[4-(1,1-dimethylethyl)phenoxy]acetoaldehyde obtained in Production Example 9 in 8 ml of methanol with stirring at a temperature of 10° C. for 30 minutes. Then the reaction mixture was further stirred at the same temperature for 30 minutes. Then, the reaction mixture was stirred under an atmosphere of a gas of ammonia at room temperature for 2 days. After the reaction was completed, the resultant mixture was poured into cold water and extracted with ethyl acetate. The residue was washed with water, dried over magnesium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel chromatography to give 3.89 g of 2-amino-3-[4-(1,1-dimethylethyl)phenoxy]propionitrile as a light-yellowish resinoid [60 MHz 1H-NMR (CDCl3, TMS), δ (ppm) 1.26(9H,s), 4.05(2H,d, J=5Hz), 4.63(1H,t, J=5Hz), 6.72(2H,d, J=10Hz), 7.21(2H,d, J=10Hz)].

Workup

stirringThen the reaction mixture was further stirred at the same temperature for 30 minutes
extractionextracted with ethyl acetate
washThe residue was washed with water
dry with materialdried over magnesium sulfate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-36e141cf3714439393cfdb4265e18758
Source dataset: uspto-grants-1995_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05411979

Reaction notes

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