Hydrogen Sulfide → 3,8-Dimethyl-5,6,7,8-tetrahydroquinoline-8-carbothioamide

HRID 436490Notes

Reaction equation

HRID 436490 reaction equation
[CH3:1][C:2]1[CH:3]=[N:4][C:5]2[C:6]([CH3:14])([C:12]#[N:13])[CH2:7][CH2:8][CH2:9][C:10]=2[CH:11]=1.[SH2:15].C(N(CC)CC)C>N1C=CC=CC=1>[CH3:1][C:2]1[CH:3]=[N:4][C:5]2[C:6]([CH3:14])([C:12](=[S:15])[NH2:13])[CH2:7][CH2:8][CH2:9][C:10]=2[CH:11]=1

Participants

5

Reactant 3

HCID 402Hydrogen SulfideHCID 8471TriethylamineHCID 123519318-Quinolinecarbonitrile, 5,6,7,8-tetrahydro-3,8-dimethyl-

Product 1

HCID 123519003,8-Dimethyl-5,6,7,8-tetrahydroquinoline-8-carbothioamide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

3,8-dimethyl-8-cyano-5,6,7,8-tetrahydroquinoline is treated with H2S in pyridine and in the presence of triethylamine following the general procedure of Example 5 and the title compound is isolated and recrystallised from benzene as the quarter hydrate, colourless needles m.p. 164° C. This was converted to the hydrochloride by treatment in isopropanol with a solution of dry HCl gas in ether. The title compound hydrochloride crystallised as colourless needles m.p. 277° C.

Sources & evidence

ORD record
ord-df69e45a02504765af8bdc46fa530f54
Source dataset
uspto-grants-1977_02
Patent number
US04009169

Reaction notes

Loading…