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

HRID 35161

Reaction equation

HRID 35161 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.[CH2:18]([S-:30])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29].[Na+]>C(S)CCCCCCCCCCC>[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:30][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])=[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 23672953Sodium dodecane-1-thiolate

Product 1

HCID 19833911dodecyl 5,7-dihydro-6H-dibenz[c,e]azepine-6-thiocarboximidate

Reagents, catalysts & solvents 1

HCID 81951-DodecanethiolSolvent

Procedure

starting from 5,7-dihydro-6H-dibenz[c,e]azepine-6-carbonitrile and sodium dodecanethiolate in 1-dodecanethiol there is obtained dodecyl 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): 0.88 (t, CH3), 1.2-2.0 (20H), 2.5 (t, SCH2), 4.43 (s, 4H), 7.3-7.7 (8H);

Sources & evidence

ORD record
ord-c0e9a35f334147d79dbd084f56ef54e6
Source dataset
uspto-grants-1988_08
Patent number
US04766115

Linked notes

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