Hydrogen Sulfide → 5,6,7,8-Tetrahydro-3-methyl-8-quinolinecarbothioamide

HRID 2083214Notes

Reaction equation

[CH3:1][C:2]1[CH:3]=[N:4][C:5]2[CH:6]([C:12]([NH2:14])=O)[CH2:7][CH2:8][CH2:9][C:10]=2[CH:11]=1.S.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:17]>N1C=CC=CC=1>[CH3:1][C:2]1[CH:3]=[N:4][C:5]2[CH:6]([C:12](=[S:17])[NH2:14])[CH2:7][CH2:8][CH2:9][C:10]=2[CH:11]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 3-methyl-5,6,7,8-tetrahydroquinoline-8-carboxamide (27.9 g. 0.14 m) in dry pyridine (300 ml.), saturated with H2S gas, was treated with P2S5 (26 g., 0.14 m) and heated at reflux for 45 min. whilst maintaining a slow stream of H2S gas. The reaction mixture was evaporated to dryness in vacuo and cooled to 0° C, made alkaline with 10% sodium hydroxide and the solution extracted with chloroform (3 × 100 ml.). The combined extracts were washed with brine, dried and evaporated in vacuo. The residual oil was triturated with benzene and the solid filtered and recrystallised from benzene to give the title compound as pale yellow needles m.p. 149° (21.8 g., 87%). The hydrochloride was prepared as already described in Example 10 and isolated as colourless needles m.p. 219° C.

Workup

temperatureheated
temperatureat reflux for 45 min.
customThe reaction mixture was evaporated to dryness in vacuo
extractionthe solution extracted with chloroform (3 × 100 ml.)
washThe combined extracts were washed with brine
customdried
customevaporated in vacuo
customThe residual oil was triturated with benzene
filtrationthe solid filtered
customrecrystallised from benzene

Sources & evidence

ORD record: ord-bace4820fed74a41bc4fe9b21681601f
Source dataset: uspto-grants-1978_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04085110

Reaction notes

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