Carbon Disulfide → 1H-Pyrrole-1-carbodithioic acid phenylmethyl ester

HRID 352703Notes

Reaction equation

HRID 352703 reaction equation
[NH:1]1[CH:5]=[CH:4][CH:3]=[CH:2]1.[H-].[Na+].[C:8](=[S:10])=[S:9].[CH2:11](Cl)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>CS(C)=O.C(OCC)C.O>[N:1]1([C:8]([S:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[S:9])[CH:5]=[CH:4][CH:3]=[CH:2]1

Participants

8

Reactant 4

HCID 6348Carbon DisulfideHCID 7503Benzyl ChlorideHCID 8027PyrroleHCID 24758Sodium hydride

Product 1

HCID 121494521H-Pyrrole-1-carbodithioic acid phenylmethyl esterYield 50.1%

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

Pyrrole (1.34 g, 20 mmol) was added dropwise to a stirred suspension of sodium hydride (0.48 g, 20 mmol) in dimethyl sulfoxide (20 mL). On completion of addition the resulting brown solution was stirred at room temperature for 30 minutes before the addition of carbon disulfide (1.52 g, 20 mmol). The solution was allowed to stir at room temperature for a further half hour and benzyl chloride (2.53 g, 20 mmol) added. Water (20 mL) was added after 1 hour followed by diethyl ether (20 mL). The organic layer was separated and the aqueous layer extracted with diethyl ether (2×20 mL). The combined extracts were dried with magnesium sulfate, filtered and the solvent removed. The crude product was chromatographed using 5% ethyl acetate in petroleum spirits to isolate the product as a yellow oil (2.34 g, 50%). 1H-nmr (CDCl3) δ 4.60 (2H), 6.30 (2H), 7.40 (5H), 7.70 (2H). 13C-nmr (CDCl3) δ 41.7, 114.2, 120.6, 128.0, 128.8, 129.4, 135.0, 189.0.

Workup

  1. additionOn completion of addition the resulting brown solution
  2. customThe organic layer was separated
  3. extractionthe aqueous layer extracted with diethyl ether (2×20 mL)
  4. dry with materialThe combined extracts were dried with magnesium sulfate
  5. filtrationfiltered
  6. customthe solvent removed
  7. customThe crude product was chromatographed

Sources & evidence

ORD record
ord-0f464493d4fd4abda51f32c826789691
Source dataset
uspto-grants-2004_06
Patent number
US06747111B2

Reaction notes

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