Methyl 3,5-dinitro-2-[(phenylmethyl)thio]benzoate → HCID 19987327, compound

HRID 2106951Notes

Reaction equation

HRID 2106951 reaction equation
[CH3:1][O:2][C:3](=[O:24])[C:4]1[CH:9]=[C:8]([N+:10]([O-])=O)[CH:7]=[C:6]([N+:13]([O-])=O)[C:5]=1[S:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>O1CCCC1.[Ni]>[CH3:1][O:2][C:3](=[O:24])[C:4]1[CH:9]=[C:8]([NH2:10])[CH:7]=[C:6]([NH2:13])[C:5]=1[S:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

4

Reactant 1

HCID 2755032Methyl 3,5-dinitro-2-[(phenylmethyl)thio]benzoate

Product 1

HCID 19987327HCID 19987327, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent

Procedure

The 2-benzylthio-3,5-dinitrobenzoic acid methyl ester obtained in the previous stage (see Example 1.14), which is still damp, is dissolved in 2 l of tetrahydrofuran and hydrogenated at from 30° to 35° C. with the addition of 3×40 g of Raney nickel. The catalyst is then removed by filtration, the filtrate is concentrated and the residue is taken up in ethyl acetate. After drying over magnesium sulfate and treating with activated carbon and fuller's earth, the filtrate is concentrated and the product is caused to crystallise by the addition of diethyl ether.

Workup

  1. customThe catalyst is then removed by filtration
  2. concentrationthe filtrate is concentrated
  3. dry with materialAfter drying over magnesium sulfate
  4. additiontreating with activated carbon and fuller's earth
  5. concentrationthe filtrate is concentrated
  6. customto crystallise by the addition of diethyl ether

Sources & evidence

ORD record
ord-dad2980fcd7a49b390cea03061b49e6b
Source dataset
uspto-grants-1990_06
Patent number
US04931581

Reaction notes

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