Hydrogen Sulfide → HCID 20189298, compound

HRID 1789026Notes

Reaction equation

HRID 1789026 reaction equation
[SH2:1].[C:2]([C:4]1[NH:5][C:6]([CH3:29])=[C:7]([C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH:8]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([N+:21]([O-:23])=[O:22])[CH:16]=2)[C:9]=1[C:10]([O:12][CH2:13][CH3:14])=[O:11])#[N:3].C(N(CC)CC)C>N1C=CC=CC=1>[NH2:3][C:2](=[S:1])[C:4]1[NH:5][C:6]([CH3:29])=[C:7]([C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH:8]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([N+:21]([O-:23])=[O:22])[CH:16]=2)[C:9]=1[C:10]([O:12][CH2:13][CH3:14])=[O:11]

Participants

5

Reactant 3

HCID 402Hydrogen SulfideHCID 8471TriethylamineHCID 13388335HCID 13388335, compound

Product 1

HCID 20189298HCID 20189298, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Hydrogen sulphide was bubbled through a solution of diethyl 2-cyano-1,4-dihydro-6-methyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylate (1 g, 2.6 mmoles) in triethylamine (0.36 ml, 2.6 mmoles) and pyridine (20 ml) at room temperature for 2 hours. The solution was degassed with nitrogen and poured into water (300 ml). After stirring for 2 hours, the precipitate was filtered off, dissolved in methylene chloride and dried (Na2SO4). The solvent was removed in vacuo and the residue triturated with CCl4 and filtered to give the title compound (0.5 g). M+ 419; (CDCl3) δ 9.3 (s,NH2), 5.2 (s,H).

Workup

  1. customThe solution was degassed with nitrogen
  2. additionpoured into water (300 ml)
  3. filtrationthe precipitate was filtered off
  4. dissolutiondissolved in methylene chloride
  5. dry with materialdried (Na2SO4)
  6. customThe solvent was removed in vacuo
  7. customthe residue triturated with CCl4
  8. filtrationfiltered

Sources & evidence

ORD record
ord-ef00e214515242c1ac00fbdfc1de8423
Source dataset
uspto-grants-1987_08
Patent number
US04686217

Reaction notes

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