Diisopropylamine → 8-Quinolinecarbothioamide, 5,6,7,8-tetrahydro-3,4-dimethyl-

HRID 1974031Notes

Reaction equation

HRID 1974031 reaction equation
C(NC(C)C)(C)C.C([Li])CCC.[CH3:13][C:14]1[CH:15]=[N:16][C:17]2[CH2:18][CH2:19][CH2:20][CH2:21][C:22]=2[C:23]=1[CH3:24].C[Si]([N:29]=[C:30]=[S:31])(C)C>C1C=CC=CC=1>[CH3:13][C:14]1[CH:15]=[N:16][C:17]2[CH:18]([C:30](=[S:31])[NH2:29])[CH2:19][CH2:20][CH2:21][C:22]=2[C:23]=1[CH3:24]

Participants

6

Reactant 4

HCID 7912DiisopropylamineHCID 75297IsothiocyanatotrimethylsilaneHCID 12278208Quinoline, 5,6,7,8-tetrahydro-3,4-dimethyl-HCID 178418339Butyllithium

Product 1

HCID 122782208-Quinolinecarbothioamide, 5,6,7,8-tetrahydro-3,4-dimethyl-Yield 5.3%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

By the method described in Example 11 using di-isopropylamine (4.9 ml 0.034 mol) in benzene (50 ml), n-butyl lithium solution (9% w/v, 25 ml, 0.034 mol), 3,4-dimethyl-5,6,7,8-tetrahydroquinoline (5.65g, 0.034 mol) and trimethylsilyl isothiocyanate (4.9 ml, 0.038 mol) was obtained 3,4-dimethyl-5,6,7,8-tetrahydroquinoline-8-thiocarboxamide (0.4 g, 5%) m.p. 163-5° C.

Sources & evidence

ORD record
ord-3ab5657469b84ed4a8944b4cc65d935b
Source dataset
uspto-grants-1976_12
Patent number
US04000142

Reaction notes

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