5,7-dihydro-6H-dibenz[c,e]azepine-6carbonitrile → 2-butyl 5,7-dihydro-6H-dibenz[c,e]azepine-6-thiocarboximidate

HRID 35162

Reaction equation

HRID 35162 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.[CH3:18][CH:19]([S-:22])[CH2:20][CH3:21].[Na+]>CC(S)CC>[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]([S:22][CH:19]([CH2:20][CH3:21])[CH3:18])=[NH:17])[CH2:6][C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 198338865,7-dihydro-6H-dibenz[c,e]azepine-6carbonitrileHCID 23677270Sodium 2-butanethiolate

Product 1

HCID 200417152-butyl 5,7-dihydro-6H-dibenz[c,e]azepine-6-thiocarboximidate

Reagents, catalysts & solvents 1

HCID 105602-ButanethiolSolvent

Procedure

starting from 5,7-dihydro-6H-dibenz[c,e]azepine-6-carbonitrile and sodium 2-butanethiolate in 2-butanethiol there is obtained 2-butyl 5,7-dihydro-6H-dibenz[c,e]azepine-6-thiocarboximidate which is purified by flash chromatography on silica gel using n-hexane/ethyl acetate (1:1) as the eluent, 1H-NMR(CDCl3): 1.05 (t, CH2CH3), 1.42 (d, CH--CH3), 1.46-1.93 (m, CH2CH3), 2.81-3.37 (m, 1H), 4.41 (s, 4H), 5.1 (broad s, NH), 7.37-7.70 (8H).

Sources & evidence

ORD record
ord-1d258d13429b4f9f9d280c93aaae0aba
Source dataset
uspto-grants-1988_08
Patent number
US04766115

Linked notes

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