4-Nitrobenzoic Acid → STK331703

HRID 990260Notes

Reaction equation

HRID 990260 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8](O)=O)=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH2:13]([SH:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:22]>C1(C)C=CC=CC=1>[CH2:13]([S:20][C:8](=[S:22])[C:7]1[CH:11]=[CH:12][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 61084-Nitrobenzoic AcidHCID 7509Benzyl mercaptanHCID 14817Phosphorus sulfide (P2S5)

Product 1

HCID 11415045STK331703Yield 51.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 4-nitrobenzoic acid (1.67 g), benzyl mercaptan (1.24 g) and phosphorus pentasulfide (4.44 g) in toluene (40 ml) was refluxed for 20 h. A dark red color was developed immediately after heating. After the reaction was complete (as monitored by GC-MS), it was cooled to room temperature and purified by a column chromatography packed with neutral alumina, eluting with benzene. Removal of the solvent by distillation gave the single compound, benzyl-4-nitrodithiobenzoate (1.48 g, 51%). It was further characterized by 1H and 13C-NMR.

Workup

  1. temperaturewas refluxed for 20 h
  2. temperatureafter heating
  3. custompurified by a column chromatography
  4. washeluting with benzene
  5. customRemoval of the solvent
  6. distillationby distillation

Sources & evidence

ORD record
ord-740fbc89090b4a61b9873d3853350b73
Source dataset
uspto-grants-2002_10
Patent number
US06458968B2

Reaction notes

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