tert-Butyl(isothiocyanato)dimethylsilane → 3,8-Dimethyl-5,6,7,8-tetrahydroquinoline-8-carbothioamide

HRID 370516Notes

Reaction equation

HRID 370516 reaction equation
[CH2:1]([Li])[CH2:2][CH2:3][CH3:4].CC1[CH:8]=[N:9][C:10]2[CH:11]([CH3:17])[CH2:12][CH2:13][CH2:14]C=2C=1.[Si]([N:25]=[C:26]=[S:27])(C(C)(C)C)(C)C>CCCCCC.O1CCCC1.C1C=CC=CC=1>[CH3:4][C:3]1[CH:8]=[N:9][C:10]2[C:11]([CH3:17])([C:26](=[S:27])[NH2:25])[CH2:12][CH2:13][CH2:14][C:1]=2[CH:2]=1

Participants

7

Reactant 3

HCID 13272319tert-Butyl(isothiocyanato)dimethylsilaneHCID 132723223,8-Dimethyl-5,6,7,8-tetrahydroquinolineHCID 178418339Butyllithium

Product 1

HCID 123519003,8-Dimethyl-5,6,7,8-tetrahydroquinoline-8-carbothioamideYield 75%

Reagents, catalysts & solvents 3

HCID 241BenzeneSolventHCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

A 1.55 molar solution of butyl lithium in hexane (12.9 ml, 20 mM) maintained below 10° was treated with a solution of 5,6,7,8-tetrahydro-3,8-dimethylquinoline (3.22 g, 20 mM) in tetrahydrofuran (10 ml). After 0.5 hours a 22% solution of t-butyldimethylsilyl isothiocyanate in benzene (13.7 g, 20 mM) was added dropwise. After a further 0.5 hours the reaction was quenched with water (100 ml.) then acidified (to pH1). After 1 hour the layers were separated, the aqueous layer basified (to pH9) and extracted with dichloromethane (2×50 ml). The organic extracts were dried and evaporated. Recrystallisation of the residue from toluene gave the title thioamide (3.3 g, 75%) mp. 160°-2°

Workup

  1. customAfter a further 0.5 hours the reaction was quenched with water (100 ml.)
  2. customAfter 1 hour the layers were separated
  3. extractionextracted with dichloromethane (2×50 ml)
  4. customThe organic extracts were dried
  5. customevaporated
  6. customRecrystallisation of the residue from toluene

Sources & evidence

ORD record
ord-3a521dfba3c6440a94ea2baa970dfd86
Source dataset
uspto-grants-1985_07
Patent number
US04526970

Reaction notes

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