Diisopropylamine → 8-Quinolinecarbothioamide, 2-butyl-5,6,7,8-tetrahydro-

HRID 1974030Notes

Reaction equation

HRID 1974030 reaction equation
C(NC(C)C)(C)C.C([Li])CCC.[CH2:13]([C:17]1[CH:26]=[CH:25][C:24]2[CH2:23][CH2:22][CH2:21][CH2:20][C:19]=2[N:18]=1)[CH2:14][CH2:15][CH3:16].C[Si]([N:31]=[C:32]=[S:33])(C)C>C1C=CC=CC=1>[CH2:13]([C:17]1[CH:26]=[CH:25][C:24]2[CH2:23][CH2:22][CH2:21][CH:20]([C:32](=[S:33])[NH2:31])[C:19]=2[N:18]=1)[CH2:14][CH2:15][CH3:16]

Participants

6

Reactant 4

HCID 7912DiisopropylamineHCID 75297IsothiocyanatotrimethylsilaneHCID 12278207HCID 12278207, compoundHCID 178418339Butyllithium

Product 1

HCID 122782198-Quinolinecarbothioamide, 2-butyl-5,6,7,8-tetrahydro-Yield 16.1%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

By the method described in Example 11 using di-isopropylamine (4.45 ml 0.03 mol) in benzene (50 ml), n-butyl lithium solution (9% w/v, 13.5 g, 0.03 mol), 2-butyl-5,6,7,8-tetrahydroquinoline (6 g, 0.03 mol) and trimethylsilyl isothiocyanate (4.45 ml 0.033 mol) was obtained 2-butyl-5,6,7,8-tetrahydroquinoline-8-thiocarboxamide (1.2g, 15%) m.p. 54-6° C. (Found: C, 68.0; H, 8.4; N, 11.2. C14H20N2S requires C, 67.8; H, 8.1; N, 11.3%).

Sources & evidence

ORD record
ord-9f6dc09c3317490fb9b117db52e6a2af
Source dataset
uspto-grants-1976_12
Patent number
US04000142

Reaction notes

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