Hydrochloric Acid → HCID 57980221, compound

HRID 1867781Notes

Reaction equation

HRID 1867781 reaction equation
[Br:1][C:2]([CH3:24])([CH3:23])[C:3]([O:5][CH2:6][CH2:7][O:8][C:9](=[O:22])[C:10]1[CH:15]=[C:14]([N+:16]([O-])=O)[CH:13]=[C:12]([N+:19]([O-])=O)[CH:11]=1)=[O:4].Cl.[Sn](Cl)Cl.[OH-].[K+]>C(O)C.O1CCCC1>[Br:1][C:2]([CH3:24])([CH3:23])[C:3]([O:5][CH2:6][CH2:7][O:8][C:9](=[O:22])[C:10]1[CH:15]=[C:14]([NH2:16])[CH:13]=[C:12]([NH2:19])[CH:11]=1)=[O:4]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 24479Stannous ChlorideHCID 57980226HCID 57980226, compound

Product 1

HCID 57980221HCID 57980221, compound

Reagents, catalysts & solvents 1

HCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

3,5-Dinitro-benzoic acid 2-(2-bromo-2-methyl-propionyloxy)-ethyl ester (9 g, 0.022 mol) was dissolved in 100 ml ethanol/tetrahydrofuran (1:1). In succession, 10N HCl (27 ml, 0.27 mol) and tin(II)chloride (50.1 g, 0.22 mol) were added. The solution was stirred at room temperature 18 h. The reaction mixture was poured into a separatory funnel containing 100 ml ice-cold water followed by the addition of 20% KOH (ice-cold, 444 g). The mixture was extracted with ether (3×100 ml). The combined organic phases were washed with water (3×100 ml) and brine, dried with solid MgSO4 and concentrated to 5.6 g.

Workup

  1. additionThe reaction mixture was poured into a separatory funnel
  2. extractionThe mixture was extracted with ether (3×100 ml)
  3. washThe combined organic phases were washed with water (3×100 ml) and brine
  4. dry with materialdried with solid MgSO4
  5. concentrationconcentrated to 5.6 g

Sources & evidence

ORD record
ord-b3a1510785fe48049476da309e85dec3
Source dataset
uspto-grants-2009_12
Patent number
US07632875B2

Reaction notes

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