Potassium Cyanide → HCID 19833971, compound

HRID 2050798Notes

Reaction equation

[CH:1]1[C:11]2[C:10]3[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=3[CH2:8][N:7]([C:16]#[N:17])[CH2:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.[OH:18][CH2:19][CH2:20][O:21][N:22]=[C:23]([CH3:25])[CH3:24].[C-]#N.[K+]>O>[CH:1]1[C:11]2[C:10]3[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=3[CH2:8][N:7]([C:16](=[NH:17])[O:18][CH2:19][CH2:20][O:21][N:22]=[C:23]([CH3:25])[CH3:24])[CH2:6][C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

Conditions

Temperature: 85 °C

Procedure

A mixture of 11.0 g of 5,7-dihydro-6H-dibenz[c,e]-azepine-6-carbonitrile, 11.7 g of acetone (2-hydroxyethyl) oxime and 0.33 g of potassium cyanide is heated to 85° C. for 3 days. The reaction mixture, cooled to about 40° C., is treated with 100 ml of water and extracted twice with ethyl acetate. The extracts are washed three times with water and once each time with semi-saturated and saturated sodium chloride solution, dried over anhydrous sodium sulfate and evaporated under reduced pressure. The residue is chromatographed on silica gel with acetone as the eluent, and there is obtained 2-[(isopropylideneamino)oxy]-ethyl 5,7-dihydro-6H-dibenz[c,e]azepine-6 carboximidate as an oil, mass spectrum m/e: M+337 (13), 281 (11), 237 (72), 194 (84), 179 (79), 165 (78), 100 (85), 56 (100).

Workup

temperatureThe reaction mixture, cooled to about 40° C.
extractionextracted twice with ethyl acetate
washThe extracts are washed three times with water
dry with materialonce each time with semi-saturated and saturated sodium chloride solution, dried over anhydrous sodium sulfate
customevaporated under reduced pressure
customThe residue is chromatographed on silica gel with acetone as the eluent

Sources & evidence

ORD record: ord-7a2211f1ab11496ebe81bf48e79b5981
Source dataset: uspto-grants-1991_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05015640

Reaction notes

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