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

HRID 1612641Notes

Reaction equation

HRID 1612641 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. Yield: 253 g (77% of the theoretical yield over three stages); m.p. 84°-86° C.

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
  7. customYield: 253 g (77% of the theoretical yield over three stages)

Sources & evidence

ORD record
ord-c29fea1cd9ed4eb3896d6c2df22a2eb0
Source dataset
uspto-grants-1993_03
Patent number
US05190928

Reaction notes

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