Hydrogen Sulfide → Ethyl 2-carbamothioylnicotinate

HRID 1400222Notes

Reaction equation

HRID 1400222 reaction equation
CCN(CC)CC.[C:8]([C:10]1[N:20]=[CH:19][CH:18]=[CH:17][C:11]=1[C:12]([O:14][CH2:15][CH3:16])=[O:13])#[N:9].[SH2:21]>N1C=CC=CC=1>[C:8]([C:10]1[N:20]=[CH:19][CH:18]=[CH:17][C:11]=1[C:12]([O:14][CH2:15][CH3:16])=[O:13])(=[S:21])[NH2:9]

Participants

5

Reactant 3

HCID 402Hydrogen SulfideHCID 8471TriethylamineHCID 12747366Ethyl 2-cyanopyridine-3-carboxylate

Product 1

HCID 86644784Ethyl 2-carbamothioylnicotinate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Et3N (10 ml) was added to a solution of ethyl 2-cyanonicotinate (1.9 g, 10.78 mmol) in 20 ml of pyridine. Hydrogen sulfide was passed through the reaction mixture at 5° C. for 20 minutes, then the mixture was stirred for 1 hour at room temperature. For work up the solution was purged with nitrogen for 30 minutes, evaporated to dryness, and the remaining solid dissolved in 200 ml of dichloromethane. The organic layer was washed successively with water and brine, dried, evaporated and treated with ethylacetate to give 2.15 g of a red oil which was reacted without further purification.

Workup

  1. customFor work up the solution was purged with nitrogen for 30 minutes
  2. customevaporated to dryness
  3. dissolutionthe remaining solid dissolved in 200 ml of dichloromethane
  4. washThe organic layer was washed successively with water and brine
  5. customdried
  6. customevaporated
  7. additiontreated with ethylacetate

Sources & evidence

ORD record
ord-5123d939dd004b7abf47a487f5fac4b0
Source dataset
uspto-grants-2014_12
Patent number
US08906941B2

Reaction notes

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