Sodium Bicarbonate → HCID 19987327, compound

HRID 1612648Notes

Reaction equation

HRID 1612648 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.C(=O)([O-])O.[Na+]>C(O)(=O)C.O1CCCC1.[Fe]>[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

6

Reactant 2

HCID 516892Sodium BicarbonateHCID 2755032Methyl 3,5-dinitro-2-[(phenylmethyl)thio]benzoate

Product 1

HCID 19987327HCID 19987327, compound

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 176Acetic AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

17.7 g of iron turnings are heated to 66° C. in 80 ml of acetic acid (5%) with thorough stirring. A solution of 12.0 g (0.034 mol) of 2-benzylthio-3,5-dinitrobenzoic acid methyl ester in 20 ml of tetrahydrofuran is then slowly added dropwise. After cooling, the batch is neutralised with saturated sodium hydrogen carbonate solution and extracted three times with ethyl acetate. The extracts are washed with water, dried over magnesium sulfate, filtered and concentrated. Crystallisation from diethyl ether gives 8.1 g (82% of the theoretical yield) of product; m.p. 80°-82° C.

Workup

  1. temperatureAfter cooling
  2. extractionextracted three times with ethyl acetate
  3. washThe extracts are washed with water
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customCrystallisation from diethyl ether
  8. customgives 8.1 g (82% of the
  9. customtheoretical yield) of product

Sources & evidence

ORD record
ord-a3ef728f928b42b49fab45656d5f1510
Source dataset
uspto-grants-1993_03
Patent number
US05190928

Reaction notes

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