Toluene → HCID 13175526, compound

HRID 434473Notes

Reaction equation

HRID 434473 reaction equation
[C:1]([C:5]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[C:8](Cl)=[C:7]([N+:15]([O-:17])=[O:16])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:18][O:19][CH:20]([O:23][CH3:24])[CH2:21][NH2:22].C1(C)C=CC=CC=1>C(OCC)C>[O:19]1[CH2:18][CH2:24][O:23][CH:20]1[CH2:21][NH:22][C:8]1[C:9]([N+:11]([O-:13])=[O:12])=[CH:10][C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])=[CH:6][C:7]=1[N+:15]([O-:17])=[O:16]

Participants

5

Reactant 3

HCID 1140TolueneHCID 751764-tert-Butyl-2,6-dinitrochlorobenzeneHCID 89728Aminoacetaldehyde dimethyl acetal

Product 1

HCID 13175526HCID 13175526, compoundYield 285.4%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

4-t-Butyl-2,6-dinitrochlorobenzene (1.8 grams; 0.007 mole), aminoacetaldehyde dimethyl acetal (1.5 grams; 0.0014 mole) and toluene (50 ml) were placed in a glass reaction vessel equipped with a stirrer, heating mantle, reflux condenser and thermometer and stirred overnight. Diethyl ether (50 ml) was added to the reaction mixture which was filtered and the filtrate then was evaporated. Toluene (50 ml), ethylene glycol (0.49 grams) and P-toluenesulfonic acid were added and the solution was refluxed for 2 hours. Then one-half the toluene was removed by distillation. The residue was chromatographed on silica to remove unreacted starting materials. The product (1.3 grams) was obtained as a yellow solid (melting point 81°-82° C.).

Workup

  1. customequipped with a stirrer
  2. temperatureheating mantle
  3. temperaturereflux condenser
  4. filtrationwas filtered
  5. customthe filtrate then was evaporated
  6. additionToluene (50 ml), ethylene glycol (0.49 grams) and P-toluenesulfonic acid were added
  7. temperaturethe solution was refluxed for 2 hours
  8. customThen one-half the toluene was removed by distillation
  9. customThe residue was chromatographed on silica
  10. customto remove unreacted

Sources & evidence

ORD record
ord-460a8ec248794684bb6a5493a31a711a
Source dataset
uspto-grants-1983_08
Patent number
US04397677

Reaction notes

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