Hydrogen Sulfide → HCID 19848484, compound

HRID 1608123Notes

Reaction equation

HRID 1608123 reaction equation
N1CCCCC1.[OH-].C([N+](C)(C)C)C1C=CC=CC=1.[CH:19]([N:21]([CH2:25][CH:26]=[CH2:27])[CH2:22][CH:23]=[CH2:24])=[O:20].[SH2:28]>CO>[CH:19]([N:21]1[CH2:25][CH:26]([CH3:27])[S:28][CH:23]([CH3:24])[CH2:22]1)=[O:20]

Participants

6

Reactant 4

HCID 402Hydrogen Sulfide2×HCID 8082PiperidineHCID 66854Benzyltrimethylammonium hydroxideHCID 246338N,N-Diallylformamide

Product 1

HCID 19848484HCID 19848484, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Piperidine (10 ml) and 10 ml of a 40% solution of benzyltrimethylammoniumhydroxide in methanol were added to a solution of N-formyl-diallylamine (55 g) in methanol (200 ml). Hydrogen sulfide (50 g) was introduced into the resulting solution, and unreacted hydrogen sulfide was kept at reflux for 7 hours by means of "cold finger". The mixture was left at room temperature for 48 hours, flushed with nitrogen, diluted with ether, and washed with water. The organic phase was dried, and the solvent evaporated in vacuo. Distillation of the residue gave the title compound with boiling point 145° C./15 mmHg.

Workup

  1. temperatureat reflux for 7 hours by means of "cold finger"
  2. customflushed with nitrogen
  3. additiondiluted with ether
  4. washwashed with water
  5. customThe organic phase was dried
  6. customthe solvent evaporated in vacuo
  7. distillationDistillation of the residue

Sources & evidence

ORD record
ord-e0c489c0daac4c04bbda3865cc1b37aa
Source dataset
uspto-grants-1989_09
Patent number
US04870063

Reaction notes

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