Pyridine → Methyl 5-sulfanylidenepyrrolidine-3-carboxylate

HRID 464629Notes

Reaction equation

HRID 464629 reaction equation
[CH3:1][O:2][C:3]([CH:5]1[CH2:9][NH:8][C:7](=O)[CH2:6]1)=[O:4].P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:12].N1C=CC=CC=1>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]([CH:5]1[CH2:9][NH:8][C:7](=[S:12])[CH2:6]1)=[O:4]

Participants

5

Reactant 3

HCID 1049PyridineHCID 14817Phosphorus sulfide (P2S5)HCID 131181175-Oxo-pyrrolidine-3-carboxylic acid methyl ester

Product 1

HCID 13118118Methyl 5-sulfanylidenepyrrolidine-3-carboxylate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

10 g of 4-methoxycarbonyl-pyrrolidine-2-one II (prepared as described in P. L. Paytash, E. Sparrow and I. C. Gathe, J. Am. Chem. Soc. 72, 1415 (1950)) were dissolved in 170 ml of absolute toluene under the influence of heat. 16.7 g of P4S10 ×4 pyridine (Riedel de Haen, Hanover, West Germany) and 42 g of kieselguhr (as a filtration aid) were then added in succession. The mixture was subsequently warmed at 90°-100° C. for 3 hours, while stirring and under nitrogen as an inert gas. The solid was then filtered off with suction and the residue on the filter was rinsed with hot toluene. The filtrate was concentrated in vacuo.

Workup

  1. temperatureof heat
  2. temperatureThe mixture was subsequently warmed at 90°-100° C. for 3 hours
  3. filtrationThe solid was then filtered off with suction
  4. washthe residue on the filter was rinsed with hot toluene
  5. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-1822b2fc8fe14a4c9b566905c18d4794
Source dataset
uspto-grants-1985_10
Patent number
US04548936

Reaction notes

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