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

HRID 1974029Notes

Reaction equation

HRID 1974029 reaction equation
C(NC(C)C)(C)C.C([Li])CCC.[CH2:13]([C:15]1[CH:24]=[CH:23][C:22]2[CH2:21][CH2:20][CH2:19][CH2:18][C:17]=2[N:16]=1)[CH3:14].C[Si]([N:29]=[C:30]=[S:31])(C)C>C1C=CC=CC=1>[CH2:13]([C:15]1[CH:24]=[CH:23][C:22]2[CH2:21][CH2:20][CH2:19][CH:18]([C:30](=[S:31])[NH2:29])[C:17]=2[N:16]=1)[CH3:14]

Participants

6

Reactant 4

HCID 7912DiisopropylamineHCID 75297IsothiocyanatotrimethylsilaneHCID 12278206HCID 12278206, compoundHCID 178418339Butyllithium

Product 1

HCID 122782188-Quinolinecarbothioamide, 2-ethyl-5,6,7,8-tetrahydro-Yield 19.5%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

By the method described in Example 11 using di-isopropylamine (2 ml 0.014 mol) in benzene (20 ml), n-butyl lithium solution (9% w/v, 10 ml, 0.014 mol), 2-ethyl-5,6,7,8-tetrahydroquinoline (2.3 g, 0.014 mol) and trimethylsilyl isothiocyanate (2 ml 0.015 mol) was obtained 2-ethyl-5,6,7,8-tetrahydroquinoline-8-thiocarboxamide (600 mg, 20%) m.p. 73-5° C (Found: C, 65.25; H, 7.6; N, 12.75. C12H16N2S requires C, 65.4; H, 7.3; N, 12.7%).

Sources & evidence

ORD record
ord-f59a7f00d1b54a2c80429917cfb37028
Source dataset
uspto-grants-1976_12
Patent number
US04000142

Reaction notes

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