Potassium Carbonate → HCID 178510539, compound

HRID 556410Notes

Reaction equation

HRID 556410 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]1[C:11](=[CH2:12])[CH2:10][CH2:9][CH2:8][C:7]1=O.[C:14]([CH2:16][C:17]([NH2:19])=[S:18])#[N:15].C(=O)([O-])[O-].[K+].[K+].[S]>CC(C)=O>[SH:18][C:17]1[C:16]([C:14]#[N:15])=[C:6]([C:2]2[S:1][CH:5]=[CH:4][CH:3]=2)[C:11]2[CH2:10][CH2:9][CH2:8][CH2:7][C:12]=2[N:19]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 14162772-CyanoethanethioamideHCID 5362487SulfurHCID 66991859HCID 66991859, compound

Product 1

HCID 178510539HCID 178510539, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

12.68 g (65.9 mmol) 2-thiophene-2-yl-methylene-cyclohexanone, 7.00 g (70.0 mmol) cyanthioacetamide and 10.00 g (72.4 mmol) potassium carbonate are refluxed in 100 ml acetone for 8 h. Then, 1.05 g (32.8 mmol) sulfur are added and refluxed for 12 h. The solvent is removed in vacuo and the residue is suspended in 600 ml ethanol/water (1:5). Following acidification with glacial acetic acid, the resulting precipitate is sucked off, washed with 200 ml water, suck dried and dried in vacuo at 50° C. 16.50 g (92%) 5,6,7,8-tetrahydro-2-mercapto-4-thiophen-2-yl-quinoline-3-carbonitrile is obtained.

Workup

  1. temperaturerefluxed for 12 h
  2. customThe solvent is removed in vacuo
  3. washwashed with 200 ml water, suck
  4. customdried
  5. customdried in vacuo at 50° C

Sources & evidence

ORD record
ord-808ef66df5a7421b880e215c9ad3cbdd
Source dataset
uspto-grants-2011_11
Patent number
US08058285B2

Reaction notes

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