Water → 4-Nitrobenzothioamide

HRID 2373768Notes

Reaction equation

HRID 2373768 reaction equation
COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:10])=CC=1.[N+:23]([C:26]1[CH:34]=[CH:33][C:29]([C:30]([NH2:32])=O)=[CH:28][CH:27]=1)([O-:25])=[O:24].O>O1CCOCC1>[N+:23]([C:26]1[CH:34]=[CH:33][C:29]([C:30](=[S:10])[NH2:32])=[CH:28][CH:27]=1)([O-:25])=[O:24]

Participants

5

Reactant 3

HCID 962WaterHCID 120914-NitrobenzamideHCID 87949Lawesson's reagent

Product 1

HCID 30005644-NitrobenzothioamideYield 119.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

6.06 g (15 mmol) of Lawesson reagent is added to a solution of 4.15 g (25 mmol) of 4-nitrobenzamide in 100 ml of 1,4-dioxan. The reaction mixture is heated under reflux for two hours. After the solution has returned to ambient temperature, it is poured into 150 ml of water and extracted with 5 times 100 ml of ethyl acetate. The organic solution is dried over magnesium sulphate, filtered and concentrated under vacuum in order to produce a yellow oil which is purified on a silica gel column (eluant: heptane/ethyl acetate 1/1). The pure fractions are collected and concentrated under vacuum. 3.26 g of a yellow powder is obtained with a yield of 72%. Melting point: 165-167° C.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureunder reflux for two hours
  3. customhas returned to ambient temperature
  4. extractionextracted with 5 times 100 ml of ethyl acetate
  5. dry with materialThe organic solution is dried over magnesium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum in order
  8. customto produce a yellow oil which
  9. customis purified on a silica gel column (eluant: heptane/ethyl acetate 1/1)
  10. customThe pure fractions are collected
  11. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-7b3e6db1e397437695c5f726bf404e58
Source dataset
uspto-grants-2008_12
Patent number
US07459558B2

Reaction notes

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