Hydrochloric Acid → 5,6,7,8-Tetrahydroquinoline-8-carbothioamide

HRID 1981630Notes

Reaction equation

HRID 1981630 reaction equation
[N:1]1[C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.[NH2-].[Li+].[Li]C1C2N=CC=CC=2CCC1.[SiH3][N:25]=[C:26]=[S:27].Cl>O>[N:1]1[C:10]2[CH:9]([C:26](=[S:27])[NH2:25])[CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 24532Lithium amideHCID 663355,6,7,8-TetrahydroquinolineHCID 139732Silyl isothiocyanateHCID 178506835HCID 178506835, compound

Product 1

HCID 122782125,6,7,8-Tetrahydroquinoline-8-carbothioamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 5,6,7,8-tetrahydroquinoline (0.01 mole) in the solvent indicated (approx. 15 ml) at 0° C. under nitrogen was treated with an alkyl lithium or a lithium amide (0.01 mole). To this solution of the 5,6,7,8-tetrahydro-8-lithioquinoline was added, at around 0° C. under nitrogen, the silyl isothiocyanate (0.01 mole) and the mixture was stirred 15 minutes. H2O(10 ml) and 2N HCl (15 ml) were added and the acid layer was separated and washed with ethyl acetate. The aqueous solution was basified (Na2CO3) and extracted with chloroform. The chloroform extracts were dried (MgSO4) and evaporated to give the 5,6,7,8-tetrahydroquinoline-8-thiocarboxamide. In this manner the thioamides in the table were prepared.

Workup

  1. customat 0° C.
  2. customthe acid layer was separated
  3. washwashed with ethyl acetate
  4. extractionextracted with chloroform
  5. dry with materialThe chloroform extracts were dried (MgSO4)
  6. customevaporated

Sources & evidence

ORD record
ord-f6bc3adccbab4a1db21d524c86e347ef
Source dataset
uspto-grants-1986_06
Patent number
US04593111

Reaction notes

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