Tetrahydrofuran → 1-(1,3-Dithiol-2-ylidene)-2-carbamoylpyrrolidinium iodide

HRID 648921Notes

Reaction equation

HRID 648921 reaction equation
O1CCCC1.[NH:6]1[CH2:13][CH2:12][CH2:11][C@H:7]1[C:8]([NH2:10])=[O:9].[I-:14].CS[C:17]1[S:21][CH:20]=[CH:19][S+:18]=1>CC(C)=O.C(OCC)C>[I-:14].[S:18]1[CH:19]=[CH:20][S:21][C:17]1=[N+:6]1[CH2:13][CH2:12][CH2:11][CH:7]1[C:8](=[O:9])[NH2:10]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 111306L-ProlinamideHCID 19751531(2H-1,3-Dithiol-2-ylidene)(methyl)sulfanium iodide

Product 1

HCID 137298241-(1,3-Dithiol-2-ylidene)-2-carbamoylpyrrolidinium iodideYield 53%

Reagents, catalysts & solvents 1

HCID 21584533Acetone diethyletherSolvent

Procedure

To 30 ml of tetrahydrofuran, 1.6 g of proline amide was dissolved, and 2.0 g of 2-methylthio-1,3-dithiolium iodide was gradually added under stirring at room temperature. The mixture was stirred at room temperature for 1 hour, and the precipitated crystals were collected by filtration and recrystallized from acetone-ethyl ether, whereby 1.3 g (yield: 53%) of 1-(1,3-dithiol-2-ylidene)-2-carbamoylpyrrolidinium iodide (Compound No. 44) was obtained as crystals having a melting point of from 250° to 251° C.

Workup

  1. stirringThe mixture was stirred at room temperature for 1 hour
  2. filtrationthe precipitated crystals were collected by filtration

Sources & evidence

ORD record
ord-3069e48ee76644c89f678b1f04d6eaa5
Source dataset
uspto-grants-1988_04
Patent number
US04737494

Reaction notes

Loading…