Sodium Sulfide → Dimethyl 4,4'-dithiobis(3-nitrobenzoate)

HRID 2306653Notes

Reaction equation

HRID 2306653 reaction equation
[S-2:1].[Na+].[Na+].[S].Cl[C:6]1[CH:15]=[CH:14][C:9]([C:10]([O:12][CH3:13])=[O:11])=[CH:8][C:7]=1[N+:16]([O-:18])=[O:17]>CO.O.CO>[N+:16]([C:7]1[CH:8]=[C:9]([CH:14]=[CH:15][C:6]=1[S:1][S:1][C:6]1[CH:15]=[CH:14][C:9]([C:10]([O:12][CH3:13])=[O:11])=[CH:8][C:7]=1[N+:16]([O-:18])=[O:17])[C:10]([O:12][CH3:13])=[O:11])([O-:18])=[O:17]

Participants

6

Reactant 3

HCID 14804Sodium SulfideHCID 735797Methyl 4-chloro-3-nitrobenzoateHCID 5362487Sulfur

Product 1

HCID 292580Dimethyl 4,4'-dithiobis(3-nitrobenzoate)Yield 65%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 22242641Methanol--water (1/1)Solvent

Procedure

A solution of sodium sulfide.nanohydrate (1.15 g, 4.9 mmol) in methanol-water (ca. 10 mL, 1:1) is warmed on a hot plate. To this solution is added elemental sulfur (150 mg, 4.6 mmol). Heating is continued for 15 min before the solution is poured into a separate solution of 1.0 g (4.6 mmol) of methyl 4-chloro-3-nitrobenzoate (see: Kuene, J. Am. Chem. Soc. 1962, 48, 837.) in MeOH (5.0 mL). The mixture is stirred for 30 min, followed by cooling in a refrigerator overnight. The solid precipitate is filtered, washed with water and methanol, and dried in vacuo at 50° C. to afford 650 mg (65%) of dimethyl 4,4′-dithio-bis-(3-nitrobenzoate) as a yellow solid: 1H NMR (400 MHz, CDCl3) δ 9.0, 8.2, 7.9, 4.0.

Workup

  1. temperatureHeating
  2. temperatureby cooling in a refrigerator overnight
  3. filtrationThe solid precipitate is filtered
  4. washwashed with water and methanol
  5. customdried in vacuo at 50° C.

Sources & evidence

ORD record
ord-af9833a7e20d4987ae7c7198ffe91b11
Source dataset
uspto-grants-2004_12
Patent number
US06828330B2

Reaction notes

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