Water → 1-(3-chloro-2-pyridinyl)-5-mercapto-1H-pyrrole-2-carbaldehyde

HRID 252011Notes

Reaction equation

HRID 252011 reaction equation
[Cl:1][C:2]1[C:3]([N:8]2[C:12]([S:13]C#N)=[CH:11][CH:10]=[C:9]2[CH:16]=[O:17])=[N:4][CH:5]=[CH:6][CH:7]=1.O.O.O.O.O.O.O.O.O.[S-2].[Na+].[Na+].O>C(O)(=O)C>[Cl:1][C:2]1[C:3]([N:8]2[C:12]([SH:13])=[CH:11][CH:10]=[C:9]2[CH:16]=[O:17])=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 73972Sodium sulfide nonahydrateHCID 866325621-(3-chloro-2-pyridinyl)-5-thiocyanato-1H-pyrrole-2-carbaldehyde

Product 1

HCID 866325651-(3-chloro-2-pyridinyl)-5-mercapto-1H-pyrrole-2-carbaldehydeYield 78.9%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 0.70 g of 1-(3-chloro-2-pyridinyl)-5-thiocyanato-1H-pyrrole-2-carbaldehyde, 0.64 g of sodium sulfide nonahydrate and 10 ml of water was stirred for 1 hour under heat refluxing. The reaction mixture was allowed to cool to room temperature, adjusted to pH 5 by an addition of acetic acid, and then extracted with ethyl acetate two times. The organic layers were combined, washed with an aqueous saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was washed with methyl tert-butyl ether to obtain 0.50 g of 1-(3-chloro-2-pyridinyl)-5-mercapto-1H-pyrrole-2-carbaldehyde of the formula:

Workup

  1. temperatureunder heat
  2. temperaturerefluxing
  3. extractionextracted with ethyl acetate two times
  4. washwashed with an aqueous saturated sodium chloride solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. washThe residue was washed with methyl tert-butyl ether

Sources & evidence

ORD record
ord-9ca6684f937747b8856550a66971b2b1
Source dataset
uspto-grants-2011_01
Patent number
US07867949B2

Reaction notes

Loading…